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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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(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

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Synthetic route

: 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

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran	94%

: 1385030-65-8
C37H66O4Si2

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
With hydrogen fluoride In tetrahydrofuran; water at 20℃; for 3h;	90%

: 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

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 2h;	2.5 mg

: 935263-58-4
8-benzenesulfonyl-2,6-dimethyl-octa-1,6-dien-3-ol

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C 5: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3CHCl3 / 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

Yield

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

: 935263-72-2
[3-(5-benzenesulfonyl-3-methyl-pent-3-enyl)-2-methyl-oxiranyl]-methanol

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C 6.1: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3CHCl3 / 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

Yield

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

: 935263-61-9
5-methyl-5-(3-methyl-4-triisopropylsilanyloxy-but-2-enyl)-cyclopent-3-ene-1,2-dione

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
Multi-step reaction with 17 steps 1: MgBr2Et2O / CH2Cl2 / 1 h / 20 °C 2: 79 percent / Cs2CO3; Bu4NI / dimethylformamide / 2.5 h / 20 °C 3: 84 percent / TBAF3H2O / 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; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C 9: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3CHCl3 / 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

Yield

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

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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: MgBr2Et2O / CH2Cl2 / 1 h / 20 °C 3.1: 79 percent / Cs2CO3; Bu4NI / dimethylformamide / 2.5 h / 20 °C 4.1: 84 percent / TBAF3H2O / 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; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C 10.1: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3CHCl3 / 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

Yield

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

: 935263-71-1
4-allyl-5-(4-hydroxy-3-methyl-but-2-enyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C 6: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3CHCl3 / 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

Yield

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

: 935263-59-5
4-allyl-5-(4-bromo-3-methyl-but-2-enyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C 5: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3CHCl3 / 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

Yield

: 935263-62-0
4-allyl-2-hydroxy-5-methyl-5-(3-methyl-4-triisopropylsilanyloxy-but-2-enyl)-cyclopent-2-enone

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
Multi-step reaction with 16 steps 1: 79 percent / Cs2CO3; Bu4NI / dimethylformamide / 2.5 h / 20 °C 2: 84 percent / TBAF3H2O / 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; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C 8: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3CHCl3 / 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; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C View Scheme

Yield

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

: 935263-65-3
2,7-dihydroxy-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3CHCl3 / 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; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C View Scheme

Yield

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

: 935263-70-0
4-allyl-2-(4-methoxy-benzyloxy)-5-methyl-5-(3-methyl-4-triisopropylsilanyloxy-but-2-enyl)-cyclopent-2-enone

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
Multi-step reaction with 15 steps 1: 84 percent / TBAF3H2O / 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; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C 7: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3CHCl3 / 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; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C View Scheme

Yield

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

: 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

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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

Yield

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

: 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

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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

Yield

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

: 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

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 93 percent / dimethyl sulfide; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C 2: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3CHCl3 / 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

Yield

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

: 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

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C 2: 93 percent / dimethyl sulfide; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C 3: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3CHCl3 / 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

Yield

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

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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

Yield

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

: 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

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C 4: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3CHCl3 / 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

Yield

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

: 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

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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

: 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

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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

: 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

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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

: 765-70-8
3-methyl-1,2-cyclopentanedione

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
Multi-step reaction with 19 steps 1.1: (R,R)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide; Bu4NCl / Pd2dba3CHCl3 / 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: MgBr2Et2O / CH2Cl2 / 1 h / 20 °C 4.1: 79 percent / Cs2CO3; Bu4NI / dimethylformamide / 2.5 h / 20 °C 5.1: 84 percent / TBAF3H2O / 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; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C 11.1: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3CHCl3 / 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; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C View Scheme

Yield

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

: 95763-61-4
3,7-dimethyl-1-(phenylsulfonyl)-8-hydroxy-2(E),6(E)-octadiene

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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; MgBr2Et2O / CH2Cl2 / 0.67 h / 20 °C 7.1: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3CHCl3 / 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

Yield

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

: 87920-55-6
10-hydroxy-4,8-dimethyldeca-4,8-dienal

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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

Yield

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

: 130790-62-4
(R,2E,6E)-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dienyl acetate

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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

Yield

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

: 147458-56-8
(4E,8E)-10-(tert-butyldimethylsilyloxy)-4,8-dimethyldeca-4,8-dienal

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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

Yield

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

: 615584-43-5
3-methyl-5-trimethylsilanyl-2,3,3a,6a-tetrahydrocyclopenta[b]furan-6-one

: 146436-22-8
(−)-terpestacin

Conditions

Conditions	Yield
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

Yield

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

: 146436-22-8
(−)-terpestacin

: 75-36-5
acetyl chloride

: 431901-65-4
terpestacin diacetate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃;	95%

: 186581-53-3, 908094-01-9
diazomethane

: 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

Conditions

Conditions	Yield
In methanol; diethyl ether Ambient temperature;	65 mg

: 67-56-1
methanol

: 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

Conditions

Conditions	Yield
With hydrogenchloride In methanol	17 mg

: 76-83-5
trityl chloride

: 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

Conditions

Conditions	Yield
With bisacodyl In dichloromethane at 37℃; for 120h;	29 mg

: 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

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane
With magnesium sulfate; toluene-4-sulfonic acid In dichloromethane Ambient temperature;	60 mg

: 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

B: C25H35(2)HO3

Conditions

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

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