Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigator	Steven V. Ley
Publication year	1982
Synthesis type	Total
Number of steps	12 (3 parts)
References	J. Chem. Soc., Chem. Commun. 1982, 1252. Tetrahedron 1985, 41, 4765.

Part 1 of 3

intermediate structure

KOt-Bu, n-BuLi

HMPA, THF

-78 °C, 80 min

intermediate structure

LiAlH4

Et2O

0 °C to RT, 60 min, 86% (2 steps)

intermediate structure

Br2, Ph3P

DMF, PhH

RT, 4 h, 59%

See the Appel Reaction

intermediate structure

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Part 2 of 3

intermediate structure

PhSeCl

Pyr

0 °C to RT, 105 min, 100%

intermediate structure

H2O2

CH2Cl2, H2O

0 °C to RT, 60 min, 96%

intermediate structure

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Part 3 of 3

intermediate structure

+

intermediate structure

CuBr.Me2S, Mg

THF

-50 °C to RT, 80 min, 58%

See the Michael Addition

intermediate structure

N-(Phenylselenyl)phthalimide, SnCl4

CH2Cl2

0 °C to RT, 2.5 h, 45%

intermediate structure

Ni (Raney)

EtOH

50 °C, 2 h, 91%

intermediate structure

LiAlH4, i-Pr2NLi

THF

-78 to -20 °C, 2.5 h, 66%

intermediate structure

N-(Phenylselenyl)phthalimide, n-Bu3P

THF

RT, 2 h, 62%

intermediate structure

Ni (Raney)

EtOH

45 °C, 20 min, 83%

intermediate structure

Zn, TiCl4, CH2Br2

CH2Cl2, THF

-40 to 0 °C, 20 h, 98%

See the Lombardo Methylenation

intermediate structure

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