Synthesis of Longifolene

Structure of Longifolene

C15H24

Principal investigatorElias J. Corey
Publication year1961
Synthesis typeTotal
Number of steps 14 (linear)
References
Part 1 of 1
intermediate structure
(CH2OH)2, TsOH
PhH
Reflux, , 66%
intermediate structure + intermediate structure
n-BuLi
Et2O, THF
RT to Reflux, 2 d, 96%
See the Wittig Reaction
intermediate structure
OsO4, Pyr
Et2O
-20 °C to RT, 26 h
intermediate structure
Pyr, TsCl
CH2Cl2
0 °C, 23 h
intermediate structure
CaCO3, LiClO4
THF
50 °C, 2.5 d, 48% (3 steps)
intermediate structure
HCl
EtOH, H2O
RT, 4 h, 100%
intermediate structure
Et3N
Ethylene Glycol
225 °C, 24 h, 8-12%
"The yield was 10-15 % brsm."
intermediate structure
  1. MeI
  2. Ph3CNa
Dioxane , Et2O
30 °C, 36 h, 59%
intermediate structure
BF3.OEt2, (CH2SH)2
RT, 90 min, 72%
intermediate structure
LiAlH4
Et2O
Reflux, 5 h, 100%
intermediate structure
NH2NH2, Na
Ethylene Glycol
190-195 °C, 16 h, 100%
intermediate structure
CrO3, MnSO4
AcOH, H2O
RT to 55 °C, 90 min, 82%
intermediate structure
MeLi
Et2O
Reflux, 3 d, 93%
intermediate structure
Pyr, SOCl2
CFCl3
0 °C, 12 min, 95%
intermediate structure