Synthesis of Hirsutene

C15H24

Principal investigator	Zhi-Xiang Yu
Publication year	2008
Synthesis type	Total
Number of steps	8 (linear)
References	J. Am. Chem. Soc. 2008, 130, 4421.

Part 1 of 1

Ph3P+CH2OMe Cl- , KOt-Bu
H2SO4 , H2O

THF

0 °C to RT, 3.5 h, 68%

See the Wittig Reaction

18-Crown-6, 																	
																						KOt-Bu

																	THF															

								-78 °C to RT, 								5.5 h, 								87%
							
								See the Still-Gennari Reaction
							
								"7:1 dr"

TBSOTf, Et3N

Et2O

0 °C, 3 h, 100%

CH2Cl2, Et2Zn

CH2Cl2

RT, 2 h, 86%

See the Simmons-Smith Reaction

[Rh(CO)2Cl]2, CO

1 atm.

Dioxane

80 °C, 48 h, 62%

ClCOCO2Me, DMAP

CH2Cl2

RT, 1 h, 92%

n-Bu3SnH, AIBN

PhMe

Reflux, 45 min, 66%

See the Barton-McCombie Reaction

Ph3P+CH3 Br-, KOt-Bu

PhH, t-BuOH

RT to Reflux, 90 min, 63%

See the Wittig Reaction

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