Synthesis of Hirsutene

C15H24

Principal investigator	Raymond L. Funk
Publication year	1984
Synthesis type	Formal
Number of steps	8 (linear)
References	J. Org. Chem. 1984, 49, 5021.

Part 1 of 1

TiCl4

																	CH2Cl2															

																								71%
							
								See the Michael Addition
							
								See the Hosomi-Sakurai Reaction

MeNHOH.HCl, NaOEt

EtOH, PhMe

Reflux, 24-36 h, 75%

See the Huisgen Cycloaddition

MeI

Pd, H2

89% (2 steps)

NaHCO3, mCPBA

CH2Cl2, H2O

50 °C, 48 h, 90%

See the Cope Elimination

HCrO3Cl.Pyr

H2, Pd

65% (2 steps)

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Remaining...

70% (1 step)

"See: Tetrahedron Lett. 1976, 17, 195."