Synthesis of Laurenene

C20H32

Principal investigator	Leo A. Paquette
Publication year	1988
Synthesis type	Formal
Number of steps	20 (linear)
References	J. Org. Chem. 1988, 53, 477.

Part 1 of 1

CuBr.Me2S

THF, Me2S

-78 to 0 °C, 6 h

See the Michael Addition

HCl

Acetone, H2O

RT, 3 d, 79% (2 steps)

See the Aldol Addition

Et3N, MsCl

CH2Cl2

0 °C, 30 min

DBU

CH2Cl2

RT, ON, 76% (2 steps)

MeLi

Et2O

-78 °C to RT, ON

HCrO3Cl.Pyr, Celite

CH2Cl2

RT, ON, 70% (2 steps)

CuBr.Me2S

THF, Me2S

-78 to 0 °C, 68%

See the Michael Addition

HCl

H2O, THF

RT, 71%

See the Aldol Addition

Pyr, ClC(S)O(p-MePh)

THF

RT, ON, 84%

200 °C, 100%

See the Chugaev Elimination

ZnI2, TMSCN

PhH

RT, 18 h, 96%

DBU, POCl3

Pyr

Reflux, 20 h, 92%

MeOH

RT, 11 h, 95%

i-Pr2NLi, HMPA

THF

-78 °C to RT, 6 h, 83%

i-Bu2AlH

PhH

RT, 60 min

K2CO3, NH2NH2

Diethylene glycol

260 °C, 19 h, 63% (2 steps)

See the Wolff-Kishner Reduction

BH3.Me2S
H2O , H2O2

THF

0 to 50 °C, 43 h

(COCl)2, 																	
																						DMSO, 																	
																						Et3N

																	CH2Cl2															

								-78 °C to RT, 								22 min, 								62% (2 steps)
							
								See the Swern Oxidation
							
								"Also isolated was the C4-ketone (10 % yield)."

TsOH

PhH

Reflux, 4 h, 78%

See the Claisen-Schmidt Condensation

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Remaining...

9% (5 steps)

"See : J. Am. Chem. Soc. 1987, 109, 6199."