Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigator	Benjamin List
Publication year	2008
Synthesis type	Total
Number of steps	12 (linear)
References	J. Am. Chem. Soc. 2008, 130, 6737.

Part 1 of 1

intermediate structure

(COCl)2, Et3N, DMSO

CH2Cl2

-78 to 0 °C, 2.5 h

See the Swern Oxidation

intermediate structure

Special reagent

CH2Cl2

0 °C, 3 h, 76% (2 steps)

See the Wittig Reaction

intermediate structure

Mg

MeOH

0 °C, 3.5 h, 88%

intermediate structure

KOH

EtOH, H2O

0 °C to RT, 24 h, 77%

intermediate structure

(COCl)2

CH2Cl2, DMF

0 °C

intermediate structure

TMSCHN2

MeCN, THF

0 °C, 4 h, 73%

intermediate structure

(Ph3P)CpRuCl

CH2Cl2

55 °C, 30 min, 52%

"Also isolated was 22% trans isomer"

intermediate structure

Pd/C, H2

1 atm

EtOAc

RT, 3 h, 91%

intermediate structure

Special reagent

DMSO

RT, 24 h, 84%

See the Aldol Addition

"95% ee"

intermediate structure

NaOH

Et2O, H2O

RT, 24 h, 99%

intermediate structure

Li
MeI

NH3, THF

-78 °C, 20 min, 75%

intermediate structure

KOt-Bu, Ph3P+CH3 Br-

PhMe

0 °C to reflux, 3 h, 87%

See the Wittig Reaction

intermediate structure

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