Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigator	Dennis P. Curran
Publication year	1985
Synthesis type	Total
Number of steps	12 (linear)
References	J. Am. Chem. Soc. 1985, 107, 1448. Tetrahedron 1985, 41, 3943.

Part 1 of 1

intermediate structure

i-Pr2NLi
TBSCl

HMPA, THF

-78 °C, 90 min

intermediate structure

CHCl3

Reflux, 5 h

See the Ireland-Claisen Rearrangement

intermediate structure

PhSeCl

CH2Cl2

-78 °C, 25 min, 75% (3 steps)

intermediate structure

H2O2

H2O, THF

0 °C, ON, 82%

intermediate structure

+

intermediate structure

Li.Naphthalene, CuBr.Me2S

THF, Me2S

-78 to -20 °C, 5.5 h

intermediate structure

Pyr.TsOH

EtOH

Reflux, 4 h, 75% (2 steps)

intermediate structure

i-Bu2AlH

THF

-78 °C to RT, 7 h, 83%

intermediate structure

Tf2O, Pyr

CH2Cl2

-10 °C, 70 min, 81%

intermediate structure

n-Bu4N+ I-

PhH

Reflux, 2 h, 75%

See the Finkelstein Reaction

intermediate structure

Trimethylsilylacetylene, n-BuLi

HMPA, THF

0 °C, 20 min

intermediate structure

n-Bu4N+ F-

THF

RT, 2 h, 75% (2 steps)

intermediate structure

n-Bu3SnH, AIBN

PhH

Reflux, 60 min, 64%

intermediate structure

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