Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigator	Michel Franck-Neumann
Publication year	1989
Synthesis type	Formal
Number of steps	10 (linear)
References	Tetrahedron Lett. 1989, 30, 3529.

Part 1 of 1

intermediate structure

+

intermediate structure

CuBr.Me2S

THF

-78 °C, 15 h

See the Michael Addition

intermediate structure

HCl

H2O, THF

40 °C, 24 h, 84% (2 steps)

See the Aldol Addition

intermediate structure

BzCl

Pyr

RT, 4 h, 90%

intermediate structure

Morpholine, TsOH

PhEt

Reflux, 24 h, 91%

intermediate structure

+

intermediate structure

Et2O

RT, 24 h, 40%

intermediate structure

HI

H2O, PhMe

RT, 4 h, 85%

intermediate structure

Pd/C, H2, Et3N

MeOH

RT, 12 h, 91%

intermediate structure

Li

NH3

30%

intermediate structure

HCrO3Cl.Pyr

CH2Cl2

RT, 30 min, 100%

intermediate structure

Report an error in this part

Remaining...

98% (1 step)

"See: Tetrahedron 1985, 41, 4765."

intermediate structure