Synthesis of Longifolene

Structure of Longifolene

C15H24

Principal investigator	Wolfgang Oppolzer
Publication year	1978
Synthesis type	Total
Number of steps	10 (linear)
References	J. Am. Chem. Soc. 1978, 100, 2583.

Part 1 of 1

intermediate structure

+

intermediate structure

Et3N

CHCl3

35 °C, 82%

intermediate structure

ClCO2Bn

Pyr

5 °C, 8 h, 88%

intermediate structure

hν

Cyclohexane

15-30 °C, 83%

See the De Mayo Reaction

intermediate structure

Pd/C, H2

3 atm

AcOH

RT, 18 h, 83%

See the De Mayo Reaction

intermediate structure

NaOt-Amyl, Ph3P+CH3 Br-

PhMe

RT, 90 min, 88%

See the Wittig Reaction

intermediate structure

CH2I2, Zn-Cu

Et2O

Reflux, 60 h, 78%

See the Simmons-Smith Reaction

intermediate structure

PtO2, H2

3 atm

AcOH

RT, 18 h, 96%

intermediate structure

i-Pr2NLi
MeI

THF

-78 °C to RT, 2 h, 94%

intermediate structure

MeLi

Et2O

48 °C, 3 h

intermediate structure

SOCl2

Pyr

0 °C, 10 min, 80% (2 steps)

intermediate structure

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