Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigator	Goverdhan Mehta
Publication year	1981
Synthesis type	Total
Number of steps	10 (linear)
References	J. Chem. Soc., Chem. Commun. 1981, 756. J. Am. Chem. Soc. 1986, 108, 3443.

Part 1 of 1

intermediate structure

+

intermediate structure

PhH

Reflux, 2 h, 90%

See the Diels-Alder Reaction

intermediate structure

hν

EtOAc

30 min, 85%

intermediate structure

0.1 mmHg

500 °C, 100%

intermediate structure

BnOBz

317 °C, 12 min, 37%

"The yield was 43 % brsm."

intermediate structure

H2, Pd/C

1.5 atm

EtOAc

RT, 20 min, 95%

intermediate structure

NaH, MeI

THF

10 °C to Reflux, 60 min, 65%

intermediate structure

NaOt-Amyl, Ph3P+CH3 Br-

PhMe

RT to Reflux, 3 h, 84%

See the Wittig Reaction

intermediate structure

LiAlH4

Et2O

RT, 45 min, 90%

intermediate structure

Imidazole , NaH
CS2
MeI

THF

Reflux, 4.5 h, 88%

intermediate structure

n-Bu3SnH

PhMe

Reflux, 6 h, 19%

See the Barton-McCombie Reaction

intermediate structure

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