Synthesis of Longifolene

Structure of Longifolene

C15H24

Principal investigatorWilliam S. Johnson
Publication year1975
Synthesis typeTotal
Number of steps 10 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
t-BuLi, (n-Bu3PCuI)4, AcCl
Et2O
-78 to 0 °C, , 84%
intermediate structure
  1. MeLi
  2. Br2
Et2O, CH2Cl2
-78 to 0 °C
intermediate structure
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
NaBH3CN, ZnBr2, TsOH
Et2O
RT, 2.5 h, 91%
intermediate structure
RuO2, HIO4, NaIO4
t-BuOH, H2O
RT, 18 h, 72%
intermediate structure
  1. i-Pr2NLi
  2. 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