Synthesis of Capnellene

Structure of Capnellene

C15H24

Principal investigatorLeo A. Paquette
Publication year1984
Synthesis typeTotal
Number of steps 12 (linear)
References
Part 1 of 1
intermediate structure
LiBr, HMPA
PhMe
Reflux, 2 h
intermediate structure intermediate structure
VinylMgBr
THF
10 °C to RT, 4.5 h, 46% (2 steps)
intermediate structure
MnO2/C
Petroleum ether
RT, 24 h, 95%
intermediate structure
P2O5
MsOH
0 °C, 2 min, 68%
intermediate structure
MeLi.LiBr, CuI
Et2O
0 °C, 30 min, 80%
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%
intermediate structure
VinylMgBr, CuI
THF
-78 °C to RT, 30 min, 55%
intermediate structure
  1. O3
  2. Me2S
MeOH
-78 °C to RT, 35 min
intermediate structure
n-Bu4N+ OH-, KOH
THF, Et2O, H2O
Reflux, 4 h, 84% (2 steps)
intermediate structure
H2, PtO2
MeOH
RT
intermediate structure
Ph3P+CH3 Br-, KOt-Bu
PhH
RT to Reflux, 21.5 h, 36% (2 steps)
See the Wittig Reaction
intermediate structure