1944-63-4

Usage

Uses

Used in Pharmaceutical Industry:
3-[(3AS,4S,7AS)-7A-METHYL-1,5-DIOXOOCTAHYDRO-1H-INDEN-4-YL]PROPIONIC ACID is used as a key intermediate for the novel and concise synthesis of 19-Nor-10-azasteroids. These are a new class of steroid 5α-reductase inhibitors, which are important for the development of pharmaceuticals targeting hormonal imbalances and related conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3-[(3AS,4S,7AS)-7A-METHYL-1,5-DIOXOOCTAHYDRO-1H-INDEN-4-YL]PROPIONIC ACID can be utilized as a building block for the creation of more complex molecules. Its unique structure and reactivity make it a valuable component in the synthesis of various organic compounds, potentially leading to new materials and applications.
Used in Research and Development:
Due to its unique structure and potential applications, 3-[(3AS,4S,7AS)-7A-METHYL-1,5-DIOXOOCTAHYDRO-1H-INDEN-4-YL]PROPIONIC ACID is also used in research and development for exploring new chemical reactions, understanding its reactivity, and identifying additional potential uses in various industries.

Synthetic route

C13H18O3 → 3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4)

Conditions	Yield
With sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene In water; tert-butyl alcohol at 20℃; for 18h;	40%

[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-magnesium chloride (62026-31-7) + C18H26O5 (74712-32-6, 88293-64-5) → 3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) + 2,2-dimethyl-6-(2-methyl-[1,3]dioxolan-2-yl)-hexan-3-one (71594-11-1) + (+)-3,3-ethylenedioxy-4,5-seco-19-norandrost-9-en-5,17-dione (24894-29-9)

Conditions	Yield
In tetrahydrofuran at -70℃; for 1h; Yield given;

(1R,3aS,4S,7aS)-4-(2-Carboxy-ethyl)-1-hydroxy-7a-methyl-5-oxo-octahydro-indene-1-carboxylic acid (37134-59-1) → 3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4)

Conditions	Yield
With sodium bismuthate In acetic acid

(S)-Halos-Parish ketone (17553-86-5) → 3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4)

Conditions	Yield
Multi-step reaction with 8 steps 1.1: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere 2.1: 1-methyl-1H-imidazole; iodine / tetrahydrofuran / 42 h / 20 °C / Inert atmosphere 3.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 3.2: 18 h / 20 °C / Inert atmosphere 4.1: palladium on activated charcoal; hydrogen 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 7.1: periodic acid / ethyl acetate / 20 °C 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1.1: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere 2.1: 1-methyl-1H-imidazole; iodine / tetrahydrofuran / 42 h / 20 °C / Inert atmosphere 3.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 3.2: 18 h / 20 °C / Inert atmosphere 4.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 7.1: periodic acid / ethyl acetate / 20 °C 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1.1: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere 2.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 3.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 3.2: 18 h / 20 °C / Inert atmosphere 4.1: palladium on activated charcoal; hydrogen 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 7.1: periodic acid / ethyl acetate / 20 °C 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1.1: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere 2.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 3.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 3.2: 18 h / 20 °C / Inert atmosphere 4.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 7.1: periodic acid / ethyl acetate / 20 °C 8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme

C23H40O4Si → 3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 4: periodic acid / ethyl acetate / 20 °C 5: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: palladium on activated charcoal; hydrogen 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 4: periodic acid / ethyl acetate / 20 °C 5: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme

C23H42O4Si → 3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 3: periodic acid / ethyl acetate / 20 °C 4: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme

C17H28O4 → 3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 2: periodic acid / ethyl acetate / 20 °C 3: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme

(1S,7aS)-1-hydroxy-7a-methyl-2,3,7,7a-tetrahydro-1H-inden-5(6H)-one (16271-49-1) → 3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4)

Conditions	Yield
Multi-step reaction with 7 steps 1.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 2.2: 18 h / 20 °C / Inert atmosphere 3.1: palladium on activated charcoal; hydrogen 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 6.1: periodic acid / ethyl acetate / 20 °C 7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme
Multi-step reaction with 7 steps 1.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 2.2: 18 h / 20 °C / Inert atmosphere 3.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 6.1: periodic acid / ethyl acetate / 20 °C 7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme
Multi-step reaction with 7 steps 1.1: 1-methyl-1H-imidazole; iodine / tetrahydrofuran / 42 h / 20 °C / Inert atmosphere 2.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 2.2: 18 h / 20 °C / Inert atmosphere 3.1: palladium on activated charcoal; hydrogen 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 6.1: periodic acid / ethyl acetate / 20 °C 7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme
Multi-step reaction with 7 steps 1.1: 1-methyl-1H-imidazole; iodine / tetrahydrofuran / 42 h / 20 °C / Inert atmosphere 2.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 2.2: 18 h / 20 °C / Inert atmosphere 3.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 6.1: periodic acid / ethyl acetate / 20 °C 7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme

C17H26O4 → 3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: periodic acid / ethyl acetate / 20 °C 2: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme

(1S,7aS)-1-((tert-butyldimethylsilyl)oxy)-7a-methyl-1,2,3,6,7,7a-hexahydro-5H-inden-5-one (149789-99-1, 126541-53-5) → 3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 18 h / 20 °C / Inert atmosphere 2.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / -35 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 5.1: periodic acid / ethyl acetate / 20 °C 6.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 18 h / 20 °C / Inert atmosphere 2.1: palladium on activated charcoal; hydrogen 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C 4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C 5.1: periodic acid / ethyl acetate / 20 °C 6.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C View Scheme

methanol (67-56-1) + 3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (3aS,7aS)-1,5-dioxo-4α-methylpropionic-3aα,4,5,6,7,7a-hexahydro-7a-methylindan (59005-87-7)

Conditions	Yield
With toluene-4-sulfonic acid for 23h;	96%
With toluene-4-sulfonic acid for 2h; Esterification; Heating;	90%

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → 1,6,6a,7,8,9,9a,9b-octahydro-6a-methyl-<6aS-(6aα,9aβ,9bα)>cyclopenta<1>benzopyran-3(2H)-7-dione (39783-27-2)

Conditions	Yield
With sodium acetate; acetic anhydride for 4h; Heating;	93%
With perchloric acid; acetic anhydride In ethyl acetate	81%
With perchloric acid; acetic anhydride In ethyl acetate	80%

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (3aS,9aS,9bS)-3a-Methyl-1,2,4,6,8,9,9a,9b-octahydro-3aH-6-aza-cyclopenta[a]naphthalene-3,7-dione (24967-14-4) + (3aS,9bS)-3a-Methyl-1,2,4,5,6,8,9,9b-octahydro-3aH-6-aza-cyclopenta[a]naphthalene-3,7-dione

Conditions	Yield
With formic acid; ammonium bicarbonate at 120℃; for 1h; Yields of byproduct given;	A 59% B n/a
With formic acid; ammonium bicarbonate at 120℃; for 1h; Yield given. Yields of byproduct given;

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (3aS,7aS)-4-ethylidene-5,6,7,7a-tetrahydro-7a-methylindan-1,5-dione

Conditions	Yield
With pyridine; copper diacetate; [bis(acetoxy)iodo]benzene In benzene for 8h; Decarboxylation; Heating;	40%

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) + pivaloyl chloride (3282-30-2) → C18H26O5 (74712-32-6, 88293-64-5)

Conditions	Yield
With triethylamine In tetrahydrofuran at -20℃; Yield given;
With triethylamine In tetrahydrofuran at -30℃; for 3.5h; Temperature; Inert atmosphere;

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → 17β-Hydroxy-5-oxo-des-A-10-aza-oestran (17261-92-6)

Conditions	Yield
With hydrogenchloride; formic acid; sodium cyanoborohydride; ammonium bicarbonate 1.) 120 deg C, 1 h, 2.) MeOH, pH 1.5-2, room temperature, 48 h; Yield given. Multistep reaction;

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → estradiol (50-28-2)

Conditions	Yield
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 78 percent / 4-DMAP / 3 h / 20 °C 6.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 11.2: 48 percent HF / acetonitrile / 20 °C 11.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C 12.1: 80 percent / TFA; Pb(OTFA)4 / 0.5 h / 20 °C View Scheme
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6.1: t-BuOK / tetrahydrofuran / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 11.2: 48 percent HF / acetonitrile / 20 °C 11.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C 12.1: 80 percent / TFA; Pb(OTFA)4 / 0.5 h / 20 °C View Scheme
Multi-step reaction with 13 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 78 percent / 4-DMAP / 3 h / 20 °C 7.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 12.2: 48 percent HF / acetonitrile / 20 °C 12.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C 13.1: 80 percent / TFA; Pb(OTFA)4 / 0.5 h / 20 °C View Scheme
Multi-step reaction with 13 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7.1: t-BuOK / tetrahydrofuran / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 12.2: 48 percent HF / acetonitrile / 20 °C 12.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C 13.1: 80 percent / TFA; Pb(OTFA)4 / 0.5 h / 20 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (3aS,4R,7aS)-7a-Methyl-4-vinyl-2,3,3a,4,7,7a-hexahydro-inden-1-one

Conditions	Yield
Multi-step reaction with 6 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 78 percent / 4-DMAP / 3 h / 20 °C 6: 65 percent / t-BuOK / tetrahydrofuran / 0 °C View Scheme
Multi-step reaction with 6 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6: t-BuOK / tetrahydrofuran / 0 °C View Scheme
Multi-step reaction with 7 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 78 percent / 4-DMAP / 3 h / 20 °C 7: 65 percent / t-BuOK / tetrahydrofuran / 0 °C View Scheme
Multi-step reaction with 7 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7: t-BuOK / tetrahydrofuran / 0 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (3aS,7aS)-7a-Methyl-4-vinyl-2,3,3a,6,7,7a-hexahydro-inden-1-one (250331-22-7)

Conditions	Yield
Multi-step reaction with 6 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 78 percent / 4-DMAP / 3 h / 20 °C 6: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C View Scheme
Multi-step reaction with 6 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6: t-BuOK / tetrahydrofuran / 0 °C View Scheme
Multi-step reaction with 7 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 78 percent / 4-DMAP / 3 h / 20 °C 7: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C View Scheme
Multi-step reaction with 7 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7: t-BuOK / tetrahydrofuran / 0 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (1S,3aS,7aS)-7a-Methyl-4-vinyl-2,3,3a,6,7,7a-hexahydro-1H-inden-1-ol (332900-29-5)

Conditions	Yield
Multi-step reaction with 7 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 78 percent / 4-DMAP / 3 h / 20 °C 6: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7: KBH4 / methanol / 1 h / 0 °C View Scheme
Multi-step reaction with 7 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6: t-BuOK / tetrahydrofuran / 0 °C 7: KBH4 / methanol / 1 h / 0 °C View Scheme
Multi-step reaction with 8 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 78 percent / 4-DMAP / 3 h / 20 °C 7: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8: KBH4 / methanol / 1 h / 0 °C View Scheme
Multi-step reaction with 8 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7: t-BuOK / tetrahydrofuran / 0 °C 8: KBH4 / methanol / 1 h / 0 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (3aS,7aS)-4α-ethenyl-5α-hydroxy-1-oxo-,4,5,6,7,7a-hexahydro-7a-methylindan (250331-20-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C View Scheme
Multi-step reaction with 5 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (3aS,7aS)-4α-ethenyl-5α-formyloxy-1-oxo-,4,5,6,7,7a-hexahydro-7a-methylindan (250331-19-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating View Scheme
Multi-step reaction with 4 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (3aS,5aR,9bS)-7-Hydroxy-3a-methyl-decahydro-6-oxa-cyclopenta[a]naphthalen-3-one

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (3aS,7aS)-1,5-dihydroxy-4α-β-propionolactone-3a,4,5,6,7,7a-hexahydro-7a-methylindan

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 85 percent / KBH4 / methanol / 0.5 h / 0 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (3aS,7aS)-4α-ethenyl-5α-methanesulfonyl-1-oxo-,4,5,6,7,7a-hexahydro-7a-methylindan (250331-21-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C View Scheme
Multi-step reaction with 6 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (3aS,7aS)-5-formyloxy-4α-(2'-iodoethyl)-1-oxo-3a,4,5,6,7,7a-hexahydro-7a-methylindan (250331-18-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (3aS,7aS)-4α-ethenyl-1-[(tert-butyldimethylsilyl)oxy]-3a-methyl-3a,6,7,7a-tetrahydro-4-indene (250331-25-0) + (η6-4-trimethylsilylthiepin-1,1-dioxide)chromium(0)

Conditions	Yield
Multi-step reaction with 8 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 78 percent / 4-DMAP / 3 h / 20 °C 6: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7: KBH4 / methanol / 1 h / 0 °C 8: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6: t-BuOK / tetrahydrofuran / 0 °C 7: KBH4 / methanol / 1 h / 0 °C 8: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C View Scheme
Multi-step reaction with 9 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 78 percent / 4-DMAP / 3 h / 20 °C 7: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8: KBH4 / methanol / 1 h / 0 °C 9: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C View Scheme
Multi-step reaction with 9 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7: t-BuOK / tetrahydrofuran / 0 °C 8: KBH4 / methanol / 1 h / 0 °C 9: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (3aS,7aS)-5-hydroxy-4α-β-propionolactone-1-[(tert-butyldimethylsilyl)oxy]-3a,4,5,6,7,7a-hexahydro-7a-methylindan

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 85 percent / KBH4 / methanol / 0.5 h / 0 °C 3: 85 percent / imidazole / dimethylformamide / 18 h / 20 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → 3-(tert-butyl-dimethyl-silanyloxy)-3a-methyl-dodecahydro-6-oxa-cyclopenta[a]naphthalen-7-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 85 percent / KBH4 / methanol / 0.5 h / 0 °C 3: 85 percent / imidazole / dimethylformamide / 18 h / 20 °C 4: DIBALH / CH2Cl2; hexane / 1 h / -78 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (3aS,7aS)-4α-ethenyl-1-oxo-5-(4'-methylbenzenesulfonyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan (250331-24-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 78 percent / 4-DMAP / 3 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 78 percent / 4-DMAP / 3 h / 20 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (3aS,7aS)-5-formyloxy-4α-(2'-iodoethylene)-1-[tert-(butyldimethyl)silyloxy]-3a,4,5,6,7,7a-hexahydro-7a-methylindan

Conditions	Yield
Multi-step reaction with 5 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 85 percent / KBH4 / methanol / 0.5 h / 0 °C 3: 85 percent / imidazole / dimethylformamide / 18 h / 20 °C 4: DIBALH / CH2Cl2; hexane / 1 h / -78 °C 5: 75 percent / I2; iodobenzene diacetate / cyclohexane / Photolysis View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → 1β-hydroxy-3-trimethylsilylestra-1,3,5(10)-triene (250331-30-7)

Conditions	Yield
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 78 percent / 4-DMAP / 3 h / 20 °C 6.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 11.2: 48 percent HF / acetonitrile / 20 °C 11.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C View Scheme
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6.1: t-BuOK / tetrahydrofuran / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 11.2: 48 percent HF / acetonitrile / 20 °C 11.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C View Scheme
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 78 percent / 4-DMAP / 3 h / 20 °C 7.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 12.2: 48 percent HF / acetonitrile / 20 °C 12.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C View Scheme
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7.1: t-BuOK / tetrahydrofuran / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: KNH(CH2)3NH2 / tetrahydrofuran / 15 h / 20 °C 12.2: 48 percent HF / acetonitrile / 20 °C 12.3: 45 percent / TFA; Et3SiH / benzene / 15 h / 20 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → 17-(tert-butyl-dimethyl-silanyloxy)-13-methyl-3-trimethylsilanyl-7,8,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene

Conditions	Yield
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 78 percent / 4-DMAP / 3 h / 20 °C 6.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6.1: t-BuOK / tetrahydrofuran / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 78 percent / 4-DMAP / 3 h / 20 °C 7.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7.1: t-BuOK / tetrahydrofuran / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → 1-[(tert-butyldimethylsilyl)oxy]-3-trimethylsilyl-9Hβ-estra-1,3,5(10),7-tetraene (250331-27-2)

Conditions	Yield
Multi-step reaction with 10 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 78 percent / 4-DMAP / 3 h / 20 °C 6.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C View Scheme
Multi-step reaction with 10 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6.1: t-BuOK / tetrahydrofuran / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C View Scheme
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 78 percent / 4-DMAP / 3 h / 20 °C 7.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C View Scheme
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7.1: t-BuOK / tetrahydrofuran / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → 17-(tert-butyl-dimethyl-silanyloxy)-13-methyl-3-trimethylsilanyl-7,11,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene

Conditions	Yield
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 78 percent / 4-DMAP / 3 h / 20 °C 6.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme
Multi-step reaction with 11 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4.1: 85 percent / K2CO3 / methanol / 20 °C 5.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6.1: t-BuOK / tetrahydrofuran / 0 °C 7.1: KBH4 / methanol / 1 h / 0 °C 8.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 10.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 10.2: NCS / tetrahydrofuran / -105 - 25 °C 10.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 11.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 78 percent / 4-DMAP / 3 h / 20 °C 7.1: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme
Multi-step reaction with 12 steps 1.1: 90 percent / p-TsOH / 2 h / Heating 2.1: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3.1: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4.1: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5.1: 85 percent / K2CO3 / methanol / 20 °C 6.1: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7.1: t-BuOK / tetrahydrofuran / 0 °C 8.1: KBH4 / methanol / 1 h / 0 °C 9.1: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10.1: 70 percent / 1,2-dichloro-ethane / UV-irradiation 11.1: t-BuOK / tetrahydrofuran / 0.25 h / -105 °C 11.2: NCS / tetrahydrofuran / -105 - 25 °C 11.3: 60 percent / t-BuOK / tetrahydrofuran / 4 h / 20 °C 12.1: potassium 3-aminopropylamide / tetrahydrofuran / 15 h / 20 °C View Scheme

3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4) → (1S,2S,5S,9S,13S)-6-[(tert-butyldimethylsilyl)oxy]-5-methyl-15-trimethylsilyl-18-thiatetracyclo[11.4.1.02,10.05,9]-10,14,16-triene-18,18-dioxide (250331-26-1)

Conditions	Yield
Multi-step reaction with 9 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 78 percent / 4-DMAP / 3 h / 20 °C 6: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 7: KBH4 / methanol / 1 h / 0 °C 8: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9: 70 percent / 1,2-dichloro-ethane / UV-irradiation View Scheme
Multi-step reaction with 9 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 82 percent / Pb(OAc)4; Cu(OAc)2; pyridine / benzene / Heating 4: 85 percent / K2CO3 / methanol / 20 °C 5: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 6: t-BuOK / tetrahydrofuran / 0 °C 7: KBH4 / methanol / 1 h / 0 °C 8: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 9: 70 percent / 1,2-dichloro-ethane / UV-irradiation View Scheme
Multi-step reaction with 10 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 78 percent / 4-DMAP / 3 h / 20 °C 7: 78 percent / t-BuOK / dimethylsulfoxide; tetrahydrofuran / 1 h / 0 °C 8: KBH4 / methanol / 1 h / 0 °C 9: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10: 70 percent / 1,2-dichloro-ethane / UV-irradiation View Scheme
Multi-step reaction with 10 steps 1: 90 percent / p-TsOH / 2 h / Heating 2: 86 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C 3: 78 percent / iodobenzene diacetate; I2 / cyclohexane / Photolysis 4: 30 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating 5: 85 percent / K2CO3 / methanol / 20 °C 6: 65 percent / Et3N / CH2Cl2 / 2 h / 0 °C 7: t-BuOK / tetrahydrofuran / 0 °C 8: KBH4 / methanol / 1 h / 0 °C 9: 80 percent / imidazole / dimethylformamide / 18 h / 20 °C 10: 70 percent / 1,2-dichloro-ethane / UV-irradiation View Scheme

Upstream product

• 62026-31-7 [3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-magnesium chloride 
• 74712-32-6 C₁₈H₂₆O₅ 
• 149789-99-1 (1S,7aS)-1-((tert-butyldimethylsilyl)oxy)-7a-methyl-1,2,3,6,7,7a-hexahydro-5H-inden-5-one 
• 16271-49-1 (1S,7aS)-1-hydroxy-7a-methyl-2,3,7,7a-tetrahydro-1H-inden-5(6H)-one 
• 17553-86-5 (S)-Halos-Parish ketone 
• 37134-59-1 (1R,3aS,4S,7aS)-4-(2-Carboxy-ethyl)-1-hydroxy-7a-methyl-5-oxo-octahydro-indene-1-carboxylic acid 

Downstream Products

• 50-28-2 estradiol 
• 250331-24-9 (3aS,7aS)-4α-ethenyl-1-oxo-5-(4'-methylbenzenesulfonyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan 

Relevant academic research and scientific papers

Synthesis of DOHNAA, a Mycobacterium tuberculosis Cholesterol CD Ring Catabolite and FadD3 Substrate

DOHNAA (2) is a key catabolite in the Mycobacterium tuberculosis (Mtb) cholesterol degradation pathway. The CoA ester of 2 has been implicated in regulation of gene transcription that is ultimately responsible for degradation of the C and D rings of cholesterol. A synthetic route to 2 is reported here, by a key DMSO-mediated Morita-Bayliss-Hillman-type alkylation of the Hajos-Parrish dione. As DOHNAA has to date only been available from microbial sources in very small quantities, the synthesis described will enable further studies of the enzymes involved in cholesterol degradation in Mtb and facilitate ongoing structure-activity studies based on this compound scaffold.

A SHORT EFFICIENT SYNTHESIS OF 19-NORANDROST-4-ENE-3,17-DIONE

A three-step conversion of 3aα-H-4α-(3'-propionic acid)-7aβ-methylhexahydro-1,5-indanedione into 19-norandrost-4-ene-3,17-dione is described.