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146436-22-8

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  • 1(3aH)-Cyclopentacyclopentadecenone,4,7,8,9,12,13,16,16a-octahydro-2,7-dihydroxy-3-[(1S)-2-hydroxy-1-methylethyl]-6,10,14,16a-tetramethyl-,(3aR,5E,7S,10E,14E,16aS)-

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  • 1(3aH)-Cyclopentacyclopentadecenone,4,7,8,9,12,13,16,16a-octahydro-2,7-dihydroxy-3-[(1S)-2-hydroxy-1-methylethyl]-6,10,14,16a-tetramethyl-,(3aR,5E,7S,10E,14E,16aS)-

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  • 1(3aH)-Cyclopentacyclopentadecenone,4,7,8,9,12,13,16,16a-octahydro-2,7-dihydroxy-3-[(1S)-2-hydroxy-1-methylethyl]-6,10,14,16a-tetramethyl-,(3aR,5E,7S,10E,14E,16aS)-

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  • 1(3aH)-Cyclopentacyclopentadecenone,4,7,8,9,12,13,16,16a-octahydro-2,7-dihydroxy-3-[(1S)-2-hydroxy-1-methylethyl]-6,10,14,16a-tetramethyl-,(3aR,5E,7S,10E,14E,16aS)-

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146436-22-8 Usage

General Description

Terpestacin is a naturally occurring chemical compound derived from fungal strains, particularly Aspergillus fumigatus. Its potential pharmacological use lies in its inhibitory effect on the FoF1-ATPase, known as a major energy-producing enzyme for various living organisms. Therefore, terpestacin has been suggested for potential antifungal, anticancer, and anti-inflammatory uses. Although research is ongoing, there's hope that it will provide advancements in treating different diseases due to these biological activities.

Check Digit Verification of cas no

The CAS Registry Mumber 146436-22-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,6,4,3 and 6 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 146436-22:
(8*1)+(7*4)+(6*6)+(5*4)+(4*3)+(3*6)+(2*2)+(1*2)=128
128 % 10 = 8
So 146436-22-8 is a valid CAS Registry Number.
InChI:InChI=1/C25H38O4/c1-16-7-6-8-17(2)13-14-25(5)20(11-10-18(3)21(27)12-9-16)22(19(4)15-26)23(28)24(25)29/h7,10,13,19-21,26-28H,6,8-9,11-12,14-15H2,1-5H3/b16-7-,17-13-,18-10-/t19-,20-,21+,25+/m1/s1

146436-22-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (1R,3Z,5S,8Z,12Z,15S)-5,17-dihydroxy-18-[(2S)-1-hydroxypropan-2-yl]-4,8,12,15-tetramethylbicyclo[13.3.0]octadeca-3,8,12,17-tetraen-16-one

1.2 Other means of identification

Product number -
Other names 1(3aH)-Cyclopentacyclopentadecenone,4,7,8,9,12,13,16,16a-octahydro-2,7-dihydroxy-3-(2-hydroxy-1-methylethyl)-6,10,14,16a-tetramethyl-,(3aR-(3(S*),3aR*,5E,7S*,10E,14E,16aS*))

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:146436-22-8 SDS

146436-22-8Synthetic route

(5E,10E,14E)-(3aR,7S,16aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-3-((S)-2-hydroxy-1-methyl-ethyl)-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one
429621-48-7

(5E,10E,14E)-(3aR,7S,16aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-3-((S)-2-hydroxy-1-methyl-ethyl)-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran94%
C37H66O4Si2
1385030-65-8

C37H66O4Si2

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
With hydrogen fluoride In tetrahydrofuran; water at 20℃; for 3h;90%
7-hydroxy-3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one
935263-74-4

7-hydroxy-3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
With dimethylsulfide; magnesium bromide In dichloromethane at 20℃; for 0.666667h;74%
With dimethylsulfide; magnesium bromide ethyl etherate In dichloromethane at -78 - 20℃; Inert atmosphere;74%
C39H46O6

C39H46O6

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 50℃; for 1h; Hydrolysis; deprotection;70%
(3E,7E,12E)-(1S,11S,15R,17S)-11,20-Dihydroxy-1,4,8,12,17-pentamethyl-19-oxa-tricyclo[13.6.0.016,20]henicosa-3,7,12-trien-21-one

(3E,7E,12E)-(1S,11S,15R,17S)-11,20-Dihydroxy-1,4,8,12,17-pentamethyl-19-oxa-tricyclo[13.6.0.016,20]henicosa-3,7,12-trien-21-one

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
With potassium carbonate In methanol at 20℃; for 2h;2.5 mg
8-benzenesulfonyl-2,6-dimethyl-octa-1,6-dien-3-ol
935263-58-4

8-benzenesulfonyl-2,6-dimethyl-octa-1,6-dien-3-ol

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
2: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
3: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
4: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
5: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
6: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
7: Cs2CO3; Bu4NI / dimethylformamide / 2 h
8: 8.7 mg / pyridine / 3 h / 20 °C
9: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
10: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
11: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
12: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
13: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
[3-(5-benzenesulfonyl-3-methyl-pent-3-enyl)-2-methyl-oxiranyl]-methanol
935263-72-2

[3-(5-benzenesulfonyl-3-methyl-pent-3-enyl)-2-methyl-oxiranyl]-methanol

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: pyridine; iodine; PPh3 / acetonitrile; diethyl ether / 2 h / 0 °C
1.2: 74 percent / water / acetonitrile; diethyl ether / 8 h / 38 °C
2.1: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
3.1: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
4.1: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
5.1: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
6.1: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
7.1: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
8.1: Cs2CO3; Bu4NI / dimethylformamide / 2 h
9.1: 8.7 mg / pyridine / 3 h / 20 °C
10.1: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
11.1: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
12.1: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
13.1: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
14.1: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
5-methyl-5-(3-methyl-4-triisopropylsilanyloxy-but-2-enyl)-cyclopent-3-ene-1,2-dione
935263-61-9

5-methyl-5-(3-methyl-4-triisopropylsilanyloxy-but-2-enyl)-cyclopent-3-ene-1,2-dione

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1: MgBr2*Et2O / CH2Cl2 / 1 h / 20 °C
2: 79 percent / Cs2CO3; Bu4NI / dimethylformamide / 2.5 h / 20 °C
3: 84 percent / TBAF*3H2O / tetrahydrofuran / 2 h / 0 °C
4: 88 percent / PPh3; CBr4 / acetonitrile / 20 °C
5: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
6: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
7: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
8: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
9: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
10: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
11: Cs2CO3; Bu4NI / dimethylformamide / 2 h
12: 8.7 mg / pyridine / 3 h / 20 °C
13: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
14: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
15: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
16: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
17: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
3-methyl-2-(1-methyl-1-triisopropylsilanyloxymethyl-allyloxy)-cyclopent-2-enone

3-methyl-2-(1-methyl-1-triisopropylsilanyloxymethyl-allyloxy)-cyclopent-2-enone

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1.1: CHCl3 / 0.5 h / 100 - 120 °C / microwave irradiation
1.2: Cs2CO3 / Pd(OAc)2 / acetonitrile / 0.5 h / 20 °C
2.1: MgBr2*Et2O / CH2Cl2 / 1 h / 20 °C
3.1: 79 percent / Cs2CO3; Bu4NI / dimethylformamide / 2.5 h / 20 °C
4.1: 84 percent / TBAF*3H2O / tetrahydrofuran / 2 h / 0 °C
5.1: 88 percent / PPh3; CBr4 / acetonitrile / 20 °C
6.1: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
7.1: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
8.1: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
9.1: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
10.1: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
11.1: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
12.1: Cs2CO3; Bu4NI / dimethylformamide / 2 h
13.1: 8.7 mg / pyridine / 3 h / 20 °C
14.1: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
15.1: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
16.1: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
17.1: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
18.1: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
4-allyl-5-(4-hydroxy-3-methyl-but-2-enyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone
935263-71-1

4-allyl-5-(4-hydroxy-3-methyl-but-2-enyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: 88 percent / PPh3; CBr4 / acetonitrile / 20 °C
2: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
3: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
4: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
5: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
6: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
7: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
8: Cs2CO3; Bu4NI / dimethylformamide / 2 h
9: 8.7 mg / pyridine / 3 h / 20 °C
10: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
11: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
12: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
13: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
14: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
4-allyl-5-(4-bromo-3-methyl-but-2-enyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone
935263-59-5

4-allyl-5-(4-bromo-3-methyl-but-2-enyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
2: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
3: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
4: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
5: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
6: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
7: Cs2CO3; Bu4NI / dimethylformamide / 2 h
8: 8.7 mg / pyridine / 3 h / 20 °C
9: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
10: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
11: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
12: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
13: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
4-allyl-2-hydroxy-5-methyl-5-(3-methyl-4-triisopropylsilanyloxy-but-2-enyl)-cyclopent-2-enone
935263-62-0

4-allyl-2-hydroxy-5-methyl-5-(3-methyl-4-triisopropylsilanyloxy-but-2-enyl)-cyclopent-2-enone

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1: 79 percent / Cs2CO3; Bu4NI / dimethylformamide / 2.5 h / 20 °C
2: 84 percent / TBAF*3H2O / tetrahydrofuran / 2 h / 0 °C
3: 88 percent / PPh3; CBr4 / acetonitrile / 20 °C
4: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
5: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
6: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
7: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
8: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
9: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
10: Cs2CO3; Bu4NI / dimethylformamide / 2 h
11: 8.7 mg / pyridine / 3 h / 20 °C
12: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
13: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
14: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
15: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
16: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
2,7-dihydroxy-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one
935263-65-3

2,7-dihydroxy-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
2: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
3: Cs2CO3; Bu4NI / dimethylformamide / 2 h
4: 8.7 mg / pyridine / 3 h / 20 °C
5: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
6: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
7: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
8: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
9: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
4-allyl-2-(4-methoxy-benzyloxy)-5-methyl-5-(3-methyl-4-triisopropylsilanyloxy-but-2-enyl)-cyclopent-2-enone
935263-70-0

4-allyl-2-(4-methoxy-benzyloxy)-5-methyl-5-(3-methyl-4-triisopropylsilanyloxy-but-2-enyl)-cyclopent-2-enone

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1: 84 percent / TBAF*3H2O / tetrahydrofuran / 2 h / 0 °C
2: 88 percent / PPh3; CBr4 / acetonitrile / 20 °C
3: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
4: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
5: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
6: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
7: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
8: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
9: Cs2CO3; Bu4NI / dimethylformamide / 2 h
10: 8.7 mg / pyridine / 3 h / 20 °C
11: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
12: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
13: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
14: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
15: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
7-hydroxy-6,10,14,16a-tetramethyl-2-(1-methyl-but-2-enyloxy)-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one
935263-66-4

7-hydroxy-6,10,14,16a-tetramethyl-2-(1-methyl-but-2-enyloxy)-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
2: Cs2CO3; Bu4NI / dimethylformamide / 2 h
3: 8.7 mg / pyridine / 3 h / 20 °C
4: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
5: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
6: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
7: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
8: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
2,7-dihydroxy-6,10,14,16a-tetramethyl-3-(1-methyl-but-2-enyl)-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one
1026157-60-7

2,7-dihydroxy-6,10,14,16a-tetramethyl-3-(1-methyl-but-2-enyl)-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: Cs2CO3; Bu4NI / dimethylformamide / 2 h
2: 8.7 mg / pyridine / 3 h / 20 °C
3: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
4: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
5: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
6: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
7: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
7-hydroxy-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one
935263-64-2

7-hydroxy-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
2: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
3: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
4: Cs2CO3; Bu4NI / dimethylformamide / 2 h
5: 8.7 mg / pyridine / 3 h / 20 °C
6: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
7: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
8: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
9: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
10: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
4-allyl-5-(10-hydroxy-3,7,11-trimethyl-dodeca-2,6,11-trienyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone
935263-63-1

4-allyl-5-(10-hydroxy-3,7,11-trimethyl-dodeca-2,6,11-trienyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
2: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
3: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
4: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
5: Cs2CO3; Bu4NI / dimethylformamide / 2 h
6: 8.7 mg / pyridine / 3 h / 20 °C
7: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
8: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
9: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
10: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
11: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
acetic acid 2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-3-(1-methyl-2-oxo-ethyl)-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester

acetic acid 2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-3-(1-methyl-2-oxo-ethyl)-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
2: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
3: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
7-hydroxy-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-3-(1-methyl-but-2-enyl)-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

7-hydroxy-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-3-(1-methyl-but-2-enyl)-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 8.7 mg / pyridine / 3 h / 20 °C
2: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
3: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
4: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
5: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
6: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
4-allyl-5-(5-benzenesulfonyl-10-hydroxy-3,7,11-trimethyl-dodeca-2,6,11-trienyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone
935263-73-3

4-allyl-5-(5-benzenesulfonyl-10-hydroxy-3,7,11-trimethyl-dodeca-2,6,11-trienyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
2: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
3: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
4: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
5: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
6: Cs2CO3; Bu4NI / dimethylformamide / 2 h
7: 8.7 mg / pyridine / 3 h / 20 °C
8: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
9: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
10: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
11: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
12: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
acetic acid 2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-3-(1-methyl-but-2-enyl)-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester
935263-67-5

acetic acid 2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-3-(1-methyl-but-2-enyl)-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
2: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
3: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
4: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
5: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
acetic acid 3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester
935263-69-7

acetic acid 3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
2: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
acetic acid 3-(2,3-dihydroxy-1-methyl-butyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester
935263-68-6

acetic acid 3-(2,3-dihydroxy-1-methyl-butyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-1-oxo-1,3a,4,7,8,9,12,13,16,16a-decahydro-cyclopentacyclopentadecen-7-yl ester

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
2: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
3: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
4: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
3-methyl-1,2-cyclopentanedione
765-70-8

3-methyl-1,2-cyclopentanedione

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 19 steps
1.1: (R,R)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide; Bu4NCl / Pd2dba3*CHCl3 / CH2Cl2 / -78 - 20 °C
1.2: 2,6-lutidine / CH2Cl2 / 16 h / -78 - 20 °C
2.1: CHCl3 / 0.5 h / 100 - 120 °C / microwave irradiation
2.2: Cs2CO3 / Pd(OAc)2 / acetonitrile / 0.5 h / 20 °C
3.1: MgBr2*Et2O / CH2Cl2 / 1 h / 20 °C
4.1: 79 percent / Cs2CO3; Bu4NI / dimethylformamide / 2.5 h / 20 °C
5.1: 84 percent / TBAF*3H2O / tetrahydrofuran / 2 h / 0 °C
6.1: 88 percent / PPh3; CBr4 / acetonitrile / 20 °C
7.1: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
8.1: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
9.1: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
10.1: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
11.1: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
12.1: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
13.1: Cs2CO3; Bu4NI / dimethylformamide / 2 h
14.1: 8.7 mg / pyridine / 3 h / 20 °C
15.1: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
16.1: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
17.1: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
18.1: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
19.1: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
3,7-dimethyl-1-(phenylsulfonyl)-8-hydroxy-2(E),6(E)-octadiene
95763-61-4

3,7-dimethyl-1-(phenylsulfonyl)-8-hydroxy-2(E),6(E)-octadiene

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: 80 percent / L-diethyl tartrate; TBHP / titanium tetraisopropoxide / CH2Cl2; decane / 20 h / -20 °C
2.1: pyridine; iodine; PPh3 / acetonitrile; diethyl ether / 2 h / 0 °C
2.2: 74 percent / water / acetonitrile; diethyl ether / 8 h / 38 °C
3.1: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
4.1: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
5.1: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
6.1: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
7.1: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
8.1: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
9.1: Cs2CO3; Bu4NI / dimethylformamide / 2 h
10.1: 8.7 mg / pyridine / 3 h / 20 °C
11.1: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
12.1: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
13.1: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
14.1: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
15.1: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
10-hydroxy-4,8-dimethyldeca-4,8-dienal
87920-55-6

10-hydroxy-4,8-dimethyldeca-4,8-dienal

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 76 percent / 2,6-lutidine / CH2Cl2 / 2 h / -78 °C
2.1: Ni(cod)2; (R)-P-ferrocenyl-P-(p-xylyl)phenylphosphine; triethylborane / ethyl acetate / 16 h / 0 °C
2.2: 2,6-lutidine / CH2Cl2 / 2 h / -78 °C
2.3: 1.05 g / NaOH / methanol / 0.17 h / 0 °C
3.1: 89 percent / N-methylmorpholine N-oxide; TPAP / CH2Cl2 / 2.5 h / 0 °C
4.1: 84 percent / aq. HCl / tetrahydrofuran / 8 h
5.1: triphenylphosphine; iodine; imidazole / benzene; diethyl ether / 0.92 h
6.1: LiHMDS / tetrahydrofuran / 1.5 h / 0 °C
7.1: 62 percent / NaH; H2O / toluene / 15 h
8.1: 72 percent / TBAF / tetrahydrofuran / 3 h
9.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C
9.2: triethylphosphite; oxygen / tetrahydrofuran / 0.75 h
10.1: 2.5 mg / potassium carbonate / methanol / 2 h / 20 °C
View Scheme
(R,2E,6E)-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dienyl acetate
130790-62-4

(R,2E,6E)-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dienyl acetate

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: potassium carbonate / methanol / 1 h / 0 - 20 °C
2.1: 1.34 g / aq. sodium periodinate / methanol / 0 °C
3.1: 76 percent / 2,6-lutidine / CH2Cl2 / 2 h / -78 °C
4.1: Ni(cod)2; (R)-P-ferrocenyl-P-(p-xylyl)phenylphosphine; triethylborane / ethyl acetate / 16 h / 0 °C
4.2: 2,6-lutidine / CH2Cl2 / 2 h / -78 °C
4.3: 1.05 g / NaOH / methanol / 0.17 h / 0 °C
5.1: 89 percent / N-methylmorpholine N-oxide; TPAP / CH2Cl2 / 2.5 h / 0 °C
6.1: 84 percent / aq. HCl / tetrahydrofuran / 8 h
7.1: triphenylphosphine; iodine; imidazole / benzene; diethyl ether / 0.92 h
8.1: LiHMDS / tetrahydrofuran / 1.5 h / 0 °C
9.1: 62 percent / NaH; H2O / toluene / 15 h
10.1: 72 percent / TBAF / tetrahydrofuran / 3 h
11.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C
11.2: triethylphosphite; oxygen / tetrahydrofuran / 0.75 h
12.1: 2.5 mg / potassium carbonate / methanol / 2 h / 20 °C
View Scheme
(4E,8E)-10-(tert-butyldimethylsilyloxy)-4,8-dimethyldeca-4,8-dienal
147458-56-8

(4E,8E)-10-(tert-butyldimethylsilyloxy)-4,8-dimethyldeca-4,8-dienal

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: Ni(cod)2; (R)-P-ferrocenyl-P-(p-xylyl)phenylphosphine; triethylborane / ethyl acetate / 16 h / 0 °C
1.2: 2,6-lutidine / CH2Cl2 / 2 h / -78 °C
1.3: 1.05 g / NaOH / methanol / 0.17 h / 0 °C
2.1: 89 percent / N-methylmorpholine N-oxide; TPAP / CH2Cl2 / 2.5 h / 0 °C
3.1: 84 percent / aq. HCl / tetrahydrofuran / 8 h
4.1: triphenylphosphine; iodine; imidazole / benzene; diethyl ether / 0.92 h
5.1: LiHMDS / tetrahydrofuran / 1.5 h / 0 °C
6.1: 62 percent / NaH; H2O / toluene / 15 h
7.1: 72 percent / TBAF / tetrahydrofuran / 3 h
8.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C
8.2: triethylphosphite; oxygen / tetrahydrofuran / 0.75 h
9.1: 2.5 mg / potassium carbonate / methanol / 2 h / 20 °C
View Scheme
3-methyl-5-trimethylsilanyl-2,3,3a,6a-tetrahydrocyclopenta[b]furan-6-one
615584-43-5

3-methyl-5-trimethylsilanyl-2,3,3a,6a-tetrahydrocyclopenta[b]furan-6-one

(−)-terpestacin
146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: tert-butyllithium / diethyl ether; tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C
1.2: CuI; dimethyl sulfide / hexane; tetrahydrofuran; diethyl ether
1.3: 54 percent / hexane; tetrahydrofuran; diethyl ether / 6 h / -40 °C
2.1: sodium borohydride / methanol / 3 h / 0 °C
3.1: 1.69 g / TBAF / tetrahydrofuran / 16 h / -78 - 20 °C
4.1: 94 percent / potassium tert-butoxide / dimethylsulfoxide / 0.25 h
5.1: 86 percent / triethylamine / tetrahydrofuran / 1 h / 20 °C
6.1: Ni(cod)2; (R)-P-ferrocenyl-P-(p-xylyl)phenylphosphine; triethylborane / ethyl acetate / 16 h / 0 °C
6.2: 2,6-lutidine / CH2Cl2 / 2 h / -78 °C
6.3: 1.05 g / NaOH / methanol / 0.17 h / 0 °C
7.1: 89 percent / N-methylmorpholine N-oxide; TPAP / CH2Cl2 / 2.5 h / 0 °C
8.1: 84 percent / aq. HCl / tetrahydrofuran / 8 h
9.1: triphenylphosphine; iodine; imidazole / benzene; diethyl ether / 0.92 h
10.1: LiHMDS / tetrahydrofuran / 1.5 h / 0 °C
11.1: 62 percent / NaH; H2O / toluene / 15 h
12.1: 72 percent / TBAF / tetrahydrofuran / 3 h
13.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C
13.2: triethylphosphite; oxygen / tetrahydrofuran / 0.75 h
14.1: 2.5 mg / potassium carbonate / methanol / 2 h / 20 °C
View Scheme
(−)-terpestacin
146436-22-8

(−)-terpestacin

acetyl chloride
75-36-5

acetyl chloride

terpestacin diacetate
431901-65-4

terpestacin diacetate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃;95%
(−)-terpestacin
146436-22-8

(−)-terpestacin

(5E,10E,14E)-(3aR,7S,16aS)-7-Hydroxy-3-((S)-2-hydroxy-1-methyl-ethyl)-2-methoxy-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

(5E,10E,14E)-(3aR,7S,16aS)-7-Hydroxy-3-((S)-2-hydroxy-1-methyl-ethyl)-2-methoxy-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

Conditions
ConditionsYield
In methanol; diethyl ether Ambient temperature;65 mg
methanol
67-56-1

methanol

(−)-terpestacin
146436-22-8

(−)-terpestacin

(5E,10E,14E)-(3aR,7S,16aS)-2-Hydroxy-3-((S)-2-hydroxy-1-methyl-ethyl)-7-methoxy-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

(5E,10E,14E)-(3aR,7S,16aS)-2-Hydroxy-3-((S)-2-hydroxy-1-methyl-ethyl)-7-methoxy-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

Conditions
ConditionsYield
With hydrogenchloride In methanol17 mg
trityl chloride
76-83-5

trityl chloride

(−)-terpestacin
146436-22-8

(−)-terpestacin

(5E,10E,14E)-(3aR,7S,16aS)-2,7-Dihydroxy-6,10,14,16a-tetramethyl-3-((S)-1-methyl-2-trityloxy-ethyl)-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

(5E,10E,14E)-(3aR,7S,16aS)-2,7-Dihydroxy-6,10,14,16a-tetramethyl-3-((S)-1-methyl-2-trityloxy-ethyl)-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

Conditions
ConditionsYield
With bisacodyl In dichloromethane at 37℃; for 120h;29 mg
(−)-terpestacin
146436-22-8

(−)-terpestacin

(2E,7E,11E)-(1R,14S,18S,21R)-16-Hydroxy-3,7,11,14,18-pentamethyl-20-oxa-tricyclo[12.6.1.017,21]henicosa-2,7,11,16-tetraen-15-one

(2E,7E,11E)-(1R,14S,18S,21R)-16-Hydroxy-3,7,11,14,18-pentamethyl-20-oxa-tricyclo[12.6.1.017,21]henicosa-2,7,11,16-tetraen-15-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane
With magnesium sulfate; toluene-4-sulfonic acid In dichloromethane Ambient temperature;60 mg
(−)-terpestacin
146436-22-8

(−)-terpestacin

A

(2E,7E,11E)-(1R,14S,18S,21R)-16-Hydroxy-3,7,11,14,18-pentamethyl-20-oxa-tricyclo[12.6.1.017,21]henicosa-2,7,11,16-tetraen-15-one

(2E,7E,11E)-(1R,14S,18S,21R)-16-Hydroxy-3,7,11,14,18-pentamethyl-20-oxa-tricyclo[12.6.1.017,21]henicosa-2,7,11,16-tetraen-15-one

B

C25H35(2)HO3

C25H35(2)HO3

Conditions
ConditionsYield
With deuteromethanol; water-d2; magnesium sulfate; toluene-4-sulfonic acid In dichloromethane Ambient temperature; Yield given. Yields of byproduct given;

146436-22-8Downstream Products

146436-22-8Relevant articles and documents

Enantioselective synthesis of (-)-terpestacin and structural revision of siccanol using catalytic stereoselective fragment couplings and macrocyclizations

Chan, Johann,Jamison, Timothy F.

, p. 10682 - 10691 (2004)

(-)-Terpestacin (1, naturally occurring enantiomer) and (+)-11-epi-terpestacin (2) were prepared using catalyst-controlled, stereoselective, intermolecular reductive coupling reactions of alkyne 9 and aldehyde 10, affording allylic alcohols 42 or 11-epi-42 in a 3:1 ratio (or 1:3 depending on the enantiomer of ligand 41a used). These stereoselective fragment couplings were instrumental in confirming that "siccanol" is not 11-epi-terpestacin but, in fact, is (-)-terpestacin itself. Several intramolecular alkyne-aldehyde reductive coupling approaches to 1 and 2 were also investigated and are discussed herein.

Enantioselective synthesis of (-)-terpestacin and (-)-fusaproliferin: Clarification of optical rotational measurements and absolute configurational assignments establishes a homochiral structural series

Myers, Andrew G.,Siu, Michael,Ren, Feng

, p. 4230 - 4232 (2002)

An enantioselective synthesis of the syncytium formation inhibitor (-)-terpestacin (1, 19 steps, 5.8% yield from the allylation product of (R,R)-pseudoephedrine propionamide, 3) and the fungal metabolite (-)-fusaproliferin (2, 21 steps, 5.3% yield from 3) in their natural configurations is described. The route employs a series of stereoselective enolate alkylation reactions to establish the initial stereogenic center, set the quaternary carbon configuration, close the 15-membered ring, and introduce the side-chain residue with proper stereocontrol. Careful analysis of our synthetic materials alongside natural samples has revealed that several errors were made in the earlier measurements of optical rotation or in the absolute stereochemical assignments of these natural products. Clarifying all discrepancies, we show here that natural terpestacin (1) is levorotatory, not dextrorotatory as originally described, but was correctly assigned as the (1S,11S,15R,23S)-enantiomer. Fusaproliferin (2) is levorotatory, as reported, but is in fact the (1S,11S,15R,23S)-enantiomer and not the antipodal configuration originally assigned. Copyright

Cyclic 1,2-Diketones as core building blocks: A strategy for the total synthesis of (-)-terpestacin

Trost, Barry M.,Dong, Guangbin,Vance, Jennifer A.

supporting information; experimental part, p. 6265 - 6277 (2010/07/20)

We report a full account of our work towards the total synthesis of (-)-terpestacin (1), a sesterterpene originally isolated from fungal strain Arthrinium sp. FA1744. Its promising anti-HIV and anti-cancer activity, as well as its novel structure, make terpestacin an attractive synthetic target. A strategy based on the unique reactivity of cyclic 1,2-diketones (diosphenols) was developed and total synthesis of 1 was achieved in 20 steps, in the longest linear sequence, from commercially available 2-hydroxy-3-methyl-2-cyclopenten-1- one. The key feature of our synthesis is the double usage of a "Pd AAA-Claisen" protocol (AAA = asymmetric allylic alkylation), first in the early stages to generate the C1 quaternary center and then in the late stages to install the side chain. In addition, a rather unusual ene-1,2-dione moiety was synthesized and utilized as an excellent Michael acceptor to attach the C15 substituent. Several possible routes towards the total synthesis have been examined and carefully evaluated. During our exploration many interesting chemoselectivity issues have been addressed, such as a highly selective ring-closing metathesis and a challenging oxidation of a disubstituted olefin in the presence of three trisubstiuted ones.

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