Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigator	Daniel D. Sternbach
Publication year	1990
Synthesis type	Total
Number of steps	22 (linear)
References	J. Org. Chem. 1990, 55, 2725.

Part 1 of 1

intermediate structure

TsOH, HC(OEt)3

EtOH

Reflux, 6 h, 95%

intermediate structure

O3
Ph3P

CH2Cl2

-78 °C to RT, ON, 100%

intermediate structure

+

intermediate structure

PhH

RT to Reflux, 6 h, 81%

See the Wittig Reaction

intermediate structure

LiAlH4

Et2O

0 °C, 6 h, 99%

intermediate structure

HCl

H2O, THF

RT, 25 min, 100%

intermediate structure

+

intermediate structure

Na2S2O4, Pyrrolidine

MeOH

RT, 24-36 h, 99%

intermediate structure

LiAlH4

THF

RT, 6 h, 93%

intermediate structure

Mesitylene

Reflux, 24 h, 70%

See the Diels-Alder Reaction

intermediate structure

CrO3, H2SO4

Acetone, H2O

0 °C, 60 min, 97%

See the Jones Oxidation

intermediate structure

O3
Me2S

CH2Cl2

-78 °C to RT, 99%

intermediate structure

Et3N, DMAP, Ac2O

CH2Cl2

RT, 4 h, 90%

intermediate structure

H2SO4, CrO3

Acetone, H2O

RT, 45 min, 95%

See the Jones Oxidation

intermediate structure

(COCl)2, DMF

PhH

RT, 2 h

intermediate structure

Special reagent

DMAP, t-BuSH

PhMe

Reflux, 45 min, 82% (2 steps)

See the Barton Decarboxylation

intermediate structure

Et3N

H2O, MeOH

RT, 60 min, 95%

intermediate structure

TMS2NK, Ph3P+CH3 Br-

THF

0 °C to RT, 30 min, 86%

See the Wittig Reaction

intermediate structure

(COCl)2, NaH

PhH

RT, 4 h

intermediate structure

Me2CuLi

Et2O

-78 to 0 °C, 60 min, 97% (2 steps)

intermediate structure

O3
Me2S

CH2Cl2

-78 °C to RT, 80%

intermediate structure

KOH, n-Bu4N+ OH-

Et2O, THF

Reflux, ON, 97%

See the Aldol Condensation

intermediate structure

H2, PtO2

1 atm

EtOAc

RT, 20 min, 100%

intermediate structure

KH, Ph3P+CH3 Br-

PhH, t-BuOH

RT to Reflux, 6 h, 93%

See the Wittig Reaction

intermediate structure

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