(1aR)-4,5,6,7,7a,7bα-Hexahydro-6β-hydroxy-7α,7aα-dimethyl-1aα-(1-methylethenyl)naphth[1,2-b]oxiren-2(1aH)-one

Base Information

• Chemical Name: (1aR)-4,5,6,7,7a,7bα-Hexahydro-6β-hydroxy-7α,7aα-dimethyl-1aα-(1-methylethenyl)naphth[1,2-b]oxiren-2(1aH)-one
• CAS No.: 88418-12-6
• Molecular Formula: C15H20O3
• Molecular Weight: 248.322
• Hs Code.: 2931900090
• Mol file: 88418-12-6.mol

Synonyms:6-hydroxyprotopine;(+)-sporogen-AO 1;(3S,4R,4aR,5R,6R)-sporogen-AO 1;sporogen AO 1;(1aR,6R,7R,7aR,7bR)-6-Hydroxy-1a-isopropenyl-7,7a-dimethyl-4,5,6,7,7a,7b-hexahydro-1aH-1-oxa-cyclopropa[a]naphthalen-2-one;(3R,4R,5R,6R,7R)-sporogen AO-1;sporogen AO-1;

Chemical Property of (1aR)-4,5,6,7,7a,7bα-Hexahydro-6β-hydroxy-7α,7aα-dimethyl-1aα-(1-methylethenyl)naphth[1,2-b]oxiren-2(1aH)-one

Chemical Property:

• Vapor Pressure: 1.73E-07mmHg at 25°C
• Boiling Point: 384.3°Cat760mmHg
• Flash Point: 141.4°C
• PSA: 49.83000
• Density: 1.17g/cm³
• LogP: 2.00630

Purity/Quality:

99% ^*data from raw suppliers

Sporogen-AO 1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Sporogen-AO 1 is a fungal metabolite originally isolated from A. oryzae that has diverse biological activities. It inhibits HIV-1 Tat transactivation in a cell-based assay with an IC50 value of 15.8 μM. Sporogen-AO 1 is cytotoxic to HeLa, KB, and NCI H187 cancer cells (IC50s = 8.3, 9, and 5.1 μM, respectively). It is active against C. albicans (MIC = 4 mM).

Technology Process of (1aR)-4,5,6,7,7a,7bα-Hexahydro-6β-hydroxy-7α,7aα-dimethyl-1aα-(1-methylethenyl)naphth[1,2-b]oxiren-2(1aH)-one

There total 34 articles about (1aR)-4,5,6,7,7a,7bα-Hexahydro-6β-hydroxy-7α,7aα-dimethyl-1aα-(1-methylethenyl)naphth[1,2-b]oxiren-2(1aH)-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

(3S,4R,4aR,5R,6R)-3,4-epoxy-4,4a,5,6,7,8-hexahydro-3-isopropenyl-4a,5-dimethyl-6-(tetrahydropyran-2-yloxy)-2(3H)-naphthalenone (111210-46-9) → (3S,4R,4aR,5R,6R)-sporogen-AO 1 (88418-12-6)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; at 45 ℃; for 1h;

Reference yield:

2,3-dimethyl-1,4-dihydroxybenzene (608-43-5) → (3S,4R,4aR,5R,6R)-sporogen-AO 1 (88418-12-6)

Guidance literature:

Multi-step reaction with 22 steps

1: 99 percent / H₂ / Raney nickel (W-7) / methanol / 4 h / 130 °C / 95616.1 Torr

2: 8N Jones chromic acid reagent / acetone / 1 h / Ambient temperature

3: p-toluenesulfonic acid monohydrate / benzene / 20 h / Heating; azeotropic removal of water

4: p-toluenesulfonic acid monohydrate, H₂O / acetone / 2 h / Heating

5: 86 percent / Na, isopropyl alcohol / toluene / 1 h / Heating

6: 85 percent / 0.5N HCl / tetrahydrofuran / 1 h / Heating

7: 97 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 20 h / Ambient temperature

8: 60 percent NaH (mineraloil) / benzene / 20 h / Ambient temperature

9: 1.)p-toluenesulfonyl chloride, pyridine / 1.) 0 deg C, 3 h, 2.) 0 deg C, 20 h

10: 1.) potassium tert-butoxide / 1.) t-BuOH, room temp., 1 h, 2.) 30 min.

11: 20percent aq. KOH / bis-(2-hydroxy-ethyl) ether / 15 h / Heating

12: acetic anhydride, CH₃CO₂Na / 1.5 h / Heating

13: diethyl ether / 1.5 h / -25 °C

14: 10percent aq. KOH / methanol / 1.5 h / Heating

15: p-toluenesulfonic acid monohydrate / methanol / 1 h / Ambient temperature

16: pyridinium p-toluenesulfonate / CH₂Cl₂ / 6 h / Ambient temperature

17: 1.) diisopropylamine, 1.53M n-butyllithium/n-hexane / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 20 min

18: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -70 deg C, 1 h, 2.) -70 deg C to 0 deg C

19: 67 percent / DDQ / diethyl ether / 4 h / Ambient temperature

20: 77 percent / 4.17M tert-butylhydroperoxide/toluene, 40percent Triton B/MeOH / tetrahydrofuran / 1 h / Ambient temperature

21: 1.) 1.53M n-butyllithium/n-hexane, 2.) Wittig reagent / 1.) 1,2-dimethoxyethane, 0 deg C, 2 h, 2.) 0 deg C, 30 min, 1,2-dimethoxyethane; 2 h, r.t.

22: 74 percent / pyridinium p-toluenesulfonate / methanol / 1 h / 45 °C

With pyridine; hydrogenchloride; methanol; tert.-butylhydroperoxide; potassium hydroxide; n-butyllithium; oxalyl dichloride; hexane; potassium tert-butylate; water; hydrogen; sodium acetate; sodium; pyridinium p-toluenesulfonate; acetic anhydride; chromic acid; N-benzyl-trimethylammonium hydroxide; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; p-toluenesulfonyl chloride; methyl (triphenylphosphoranylidene)acetate; isopropyl alcohol; toluene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Raney nickel (W-7); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene; diethylene glycol; benzene;

Reference yield:

(2R,3R,4R)-(-)-4-(tert-butyldimethylsiloxy)-2,3-dimethylcyclohexanone (122052-53-3) → (3S,4R,4aR,5R,6R)-sporogen-AO 1 (88418-12-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 6.2 mmol / hexamethyldisilazane / CH₂Cl₂ / 1 h / Ambient temperature

2: 58 percent / BF₃*OEt₂ / propan-2-ol; nitromethane / 2 h / -20 °C

3: 79 percent / pyrrolidine / benzene / 2 h / Heating

4: 1.) LDA / 1.) -78 deg C, THF, 1.5 h, 2.) -78 deg C, THF, 15 min

5: 1.) SO₃*Py, DMSO, 2.) Et₃N

6: 70 percent / 4.17M t-BuOOH, 40percent triton B / tetrahydrofuran; toluene; methanol / Ambient temperature

7: 0.27 mmol / diethyl ether; tetrahydrofuran / 0.08 h / 0 °C

8: 1.) conc H₂SO₄, 2.) 48percent HF / 1.) THF, 3 d, room temp., 2.) CH₃CN, 30 min, room temp.

With pyrrolidine; tert.-butylhydroperoxide; pyridine-SO₃ complex; sulfuric acid; boron trifluoride diethyl etherate; hydrogen fluoride; N-benzyl-trimethylammonium hydroxide; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; nitromethane; dichloromethane; isopropyl alcohol; toluene; benzene;

DOI:10.1016/S0040-4020(01)86136-6

upstream raw materials:

(1aS,6R,7R,7aR,7bR)-6-(tert-Butyl-dimethyl-silanyloxy)-1a-(1-hydroxy-1-methyl-2-trimethylsilanyl-ethyl)-7,7a-dimethyl-4,5,6,7,7a,7b-hexahydro-1aH-1-oxa-cyclopropa[a]naphthalen-2-one

(3S,4R,4aR,5R,6R)-3,4-epoxy-4,4a,5,6,7,8-hexahydro-3-isopropenyl-4a,5-dimethyl-6-(tetrahydropyran-2-yloxy)-2(3H)-naphthalenone

2-methylcyclohexane-1,3-dione

2,3-dimethylcyclohex-2-en-1-one

Downstream raw materials:

(1aS,6R,7R,7aR,7bR)-6-Hydroxy-7,7a-dimethyl-1a-((S)-2-methyl-oxiranyl)-4,5,6,7,7a,7b-hexahydro-1aH-1-oxa-cyclopropa[a]naphthalen-2-one

(+)-gigantenone

(+)-phaseolinone

(3R,4R,5R,6R,7R)-phomenone

Refernces

• 1、 Kitahara, Takeshi,Kurata, Hitoshi,Mori, Kenji. "EFFICIENT SYNTHESIS OF NATURAL ENANTIOMER OF SPOROGEN-AO 1 (13-DESOXYPHOMENONE), A SPOROGENIC SESQUITERPENE FROM ASPERGILLUS ORYZAE". . p. 4339 - 4350. Retrieved 2007/10/02.