Synthesis of Longifolene

Structure of Longifolene

C15H24

Principal investigator	William S. Johnson
Publication year	1975
Synthesis type	Total
Number of steps	10 (linear)
References	J. Am. Chem. Soc. 1975, 97, 4777.

Part 1 of 1

intermediate structure

+

intermediate structure

AcCl, (n-Bu3PCuI)4, t-BuLi

Et2O

-78 to 0 °C, 84%

See the Michael Addition

intermediate structure

MeLi
Br2

CH2Cl2, Et2O

-78 to 0 °C

intermediate structure

Special reagent

Acetone

RT, 60 min, 76% (2 steps)

intermediate structure

LiAlH4

Et2O

0 °C, 60 min, 92%

intermediate structure

CF3CO2H

Et2O

0 °C, 3 min, 75%

intermediate structure

ZnBr2, TsOH, NaBH3CN

Et2O

RT, 2.5 h, 91%

intermediate structure

RuO2, NaIO4, HIO4

H2O, t-BuOH

RT, 18 h, 72%

See the Lemieux-Johnson Oxidation

intermediate structure

i-Pr2NLi
MeI

THF

-78 °C to RT, 2 h, 84%

"The yield was 90 % brsm."

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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