Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigator	R. Daniel Little
Publication year	1983
Synthesis type	Formal
Number of steps	16 (linear)
References	J. Org. Chem. 1983, 48, 3139. J. Am. Chem. Soc. 1981, 103, 2744. J. Org. Chem. 1984, 49, 1849.

Part 1 of 1

intermediate structure

NaBH4

THF

0 °C to RT, 3.5 h, 61%

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i-Bu2AlH

Et2O

-20 °C, 90 min, 76%

intermediate structure

Ph3P=CH2

See the Wittig Reaction

"No yield reported."

intermediate structure

HCrO3Cl.Pyr, Celite

CH2Cl2

"No yield reported."

intermediate structure

+

intermediate structure

Et2NH

MeOH

5 °C to RT, 2 h, 77%

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+

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Et2O

0 °C, 60 min, 100%

See the Diels-Alder Reaction

intermediate structure

Special reagent

AcOH

CH2Cl2

"No yield reported."

intermediate structure

LiClO4, K3Fe(CN)6

-1.76 V vs Ag/AgCl

DMF, H2O

0 °C to RT, 2 h, 55%

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THF

Reflux, 6 h, 63%

"Also isolated was the C6-epimer (13 % yield)."

intermediate structure

BH3.THF

THF

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Celite, HCrO3Cl.Pyr

CH2Cl2

61% (2 steps)

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NaOMe, HCO2Et

PhH

0 °C to RT, 20 h, 97%

See the Claisen Condensation

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TsOH, MgSO4, n-BuSH

PhH

Reflux, 20 h, 82%

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KOt-Bu, MeI

t-BuOH

0 °C to reflux, 30 min, 50%

"The yield was 59% BRSM."

intermediate structure

KOH

Ethylene Glycol, H2O

Reflux, 24 h, 51%

intermediate structure

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Remaining...

70% (1 step)

"See: Tetrahedron Lett. 1976, 17, 195."

intermediate structure