Synthesis of Capnellene

Structure of Capnellene

C15H24

Principal investigator	Leo A. Paquette
Publication year	1984
Synthesis type	Total
Number of steps	12 (linear)
References	Can. J. Chem. 1984, 62, 2415.

Part 1 of 1

intermediate structure

LiBr, HMPA

PhMe

Reflux, 2 h

See the Semi-Pinacol Rearrangement

intermediate structure

intermediate structure

VinylMgBr

THF

10 °C to RT, 4.5 h, 46% (2 steps)

See the Grignard Reaction

intermediate structure

MnO2/C

Petroleum ether

RT, 24 h, 95%

intermediate structure

P2O5

MsOH

0 °C, 2 min, 68%

See the Nazarov Cyclization Reaction

intermediate structure

CuI, MeLi.LiBr

Et2O

0 °C, 30 min, 80%

See the Michael Addition

intermediate structure

C2H2, n-BuLi

THF

-78 to -20 °C, 15 min, 71%

"The yield was 78 & brsm."

intermediate structure

H2SO4

HCO2H

92 °C, 15 min, 89%

See the Rupe Rearrangement

intermediate structure

VinylMgBr, CuI

THF

-78 °C to RT, 30 min, 55%

See the Michael Addition

intermediate structure

O3
Me2S

MeOH

-78 °C to RT, 35 min

intermediate structure

n-Bu4N+ OH-, KOH

Et2O, H2O, THF

Reflux, 4 h, 84% (2 steps)

See the Aldol Condensation

intermediate structure

PtO2, H2

1 atm

MeOH

RT

intermediate structure

KOt-Bu, Ph3P+CH3 Br-

PhH

RT to Reflux, 21.5 h, 36% (2 steps)

See the Wittig Reaction

intermediate structure

Report an error in this part