Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigator	Shigeo Nozoe
Publication year	1976
Synthesis type	Total
Number of steps	11 (linear)
References	Tetrahedron Lett. 1976, 17, 195.

Part 1 of 1

intermediate structure

NaH, AllylCl

DME

71%

intermediate structure

Ph3P=CH2

See the Wittig Reaction

intermediate structure

240 °C, 83% (2 steps)

See the Cope Rearrangement

intermediate structure

Pyr, OsO4

Et2O

-78 °C

intermediate structure

NaIO4

H2O, THF

50% (2 steps)

intermediate structure

Ag2O, NaOH

H2O, THF

RT, 80%

See the Tollens Oxidation

intermediate structure

Pyr, (COCl)2

PhH

intermediate structure

SnCl4

CS2

30 °C, 20% (2 steps)

intermediate structure

Li

Et2O, NH3, t-BuOH

intermediate structure

CrO3.2Pyr

60% (2 steps)

See the Sarett Oxidation

intermediate structure

Ph3P=CH2

DMSO

70%

See the Wittig Reaction

intermediate structure

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