Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigator	Janine Cossy
Publication year	1987
Synthesis type	Total
Number of steps	9 (linear)
References	Tetrahedron Lett. 1987, 28, 4547. Tetrahedron 1990, 46, 1859.

Part 1 of 1

intermediate structure

+

intermediate structure

Pd(OAc)2, P(Oi-Pr)3

PhMe

Reflux, 20 h, 60%

intermediate structure

Pd(OAc)2, CH2N2

Et2O

0 °C, 30 min, 99%

intermediate structure

PtO2, NaOAc, H2

1 atm

AcOH

RT, 20 h, 82%

intermediate structure

+

intermediate structure

KH

DME

-70 to 0 °C, 3 h, 71%

intermediate structure

LiAlH4

Et2O

0 °C, 60 min, 90%

intermediate structure

KH

1,3-Diaminopropane

0 °C, 60 min, 86%

See the Alkyne Zipper Reaction

intermediate structure

HCrO3Cl.Pyr

3 Å MS

CH2Cl2

RT, 4 h, 96%

intermediate structure

Et3N

hν

MeCN

RT, 2.5 h, 58%

intermediate structure

MeMgBr, (Ph3P)2NiCl2

PhH

Reflux, 66 h, 35%

intermediate structure

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