Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigator	Tomas Hudlicky
Publication year	1980
Synthesis type	Formal
Number of steps	10 (linear)
References	J. Am. Chem. Soc. 1980, 102, 6351. J. Org. Chem. 1980, 45, 5020.

Part 1 of 1

intermediate structure

LiBr, HMPA

PhMe

Reflux, 35 min

See the Semi-Pinacol Rearrangement

intermediate structure

VinylMgBr

THF

0 °C to RT, 3 h, 90% (2 steps)

See the Grignard Reaction

intermediate structure

MeC(OMe)3, Hg(OAc)2

EtCO2H

Reflux, 18 h

See the Johnson-Claisen Rearrangement

intermediate structure

KOH

EtOH, H2O

Reflux, 2 h, 82% (2 steps)

intermediate structure

(COCl)2

Hexane(s)

Reflux, 60 min

intermediate structure

CH3CHN2

Et2O

RT, 60 min, 95% (2 steps)

intermediate structure

Cu(acac)2

PhH

Reflux, 12 h, 97%

intermediate structure

PbCO3

0.1 mmHg

580 °C, 66%

"Also isolated was the C11 epimer (11 % yield)."

intermediate structure

H2, Pd/C

3.5 atm

Hexane(s)

RT, 8 h, 97%

intermediate structure

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Remaining...

70% (1 step)

"See: <i>Tetrahedron Lett. 1976, 17, 195."

intermediate structure