Synthesis of Longifolene

Structure of Longifolene

C15H24

Principal investigatorWolfgang Oppolzer
Publication year1978
Synthesis typeTotal
Number of steps 10 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
Et3N
CHCl3
35 °C, , 82%
intermediate structure
ClCO2Bn
Pyr
5 °C, 8 h, 88%
intermediate structure
Cyclohexane
15-30 °C, , 83%
intermediate structure
H2, Pd/C
AcOH
RT, 18 h, 83%
intermediate structure
Ph3P+CH3 Br-, NaOt-Amyl
PhMe
RT, 90 min, 88%
See the Wittig Reaction
intermediate structure
Zn-Cu, CH2I2
Et2O
Reflux, 60 h, 78%
intermediate structure
H2, PtO2
AcOH
RT, 18 h, 96%
intermediate structure
  1. i-Pr2NLi
  2. 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