Synthesis of Laurenene

C20H32

Principal investigator	Michael T. Crimmins
Publication year	1987
Synthesis type	Total
Number of steps	27 (linear)
References	J. Am. Chem. Soc. 1987, 109, 6199.

Part 1 of 1

HMPA, (n-Bu3PCuI)4

THF

-50 °C to RT, 3 h, 60%

See the Michael Addition

HCl

Acetone, H2O

RT, 6 h

NaOMe

MeOH

0 °C, 30 min

See the Knoevenagel Condensation

Me2CuLi

Et2O

-78 °C, 30 min

See the Michael Addition

LiCl

DMSO, H2O

140 °C, 15 min, 71% (4 steps)

See the Krapcho Decarboxylation

(CH2OH)2, TsOH

PhH

80 °C, 5 h

n-Bu4N+ F-, KF

MeCN

80 °C, 2 h

n-BuLi, CO2

THF

-78 °C

CH2N2

Et2O

90 & (4 steps)

Me2CuLi

Et2O

-78 °C, 30 min

See the Michael Addition

HCl

Acetone, H2O

RT, 6 h, 89% (2 steps)

n-Bu4N+ F-, TMSCH2CO2Et

THF

-78 °C to RT, 2 h

1,4-Benzoquinone, 																	
																						Pd(OAc)2

																	MeCN															

								RT, 								6 h, 								80% (2 steps)
							
								See the Saegusa-Ito Oxidation
							
								"The yield was 89 % brsm."

hν

PhCl

110 °C, 87%

LiAlH4

Et2O

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C

See the Swern Oxidation

CH2Cl2

40 °C, 60 min, 89 % (3 steps)

See the Wittig Reaction

Et2O, NH3

-33 °C, 5 min

H2, Pd/C

EtOH

80% (2 steps)

LiAlH4

Et2O

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C

TsOH

PhH

80 °C, 75% (3 steps)

See the Claisen-Schmidt Condensation

NaBH4, 																	
																						CeCl3

																	MeOH															

																								23%
							
								See the Luche Reduction
							
								"Also isolated was the C13-epimer (67 % yield)."

KH, n-Bu3SnCH2I

THF

n-BuLi

Hexane(s)

0 °C, 57% (2 steps)

See the Wittig Rearrangement-[2,3]

TsCl

Pyr

LiBHEt3

THF

72% (2 steps)

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