Synthesis of Longifolene

Structure of Longifolene

C15H24

Principal investigatorJohn E. McMurry
Publication year1972
Synthesis typeTotal
Number of steps 18 (linear)
References
Part 1 of 1
intermediate structure
(CH2OH)2, TsOH
PhH
Reflux, 25 min
intermediate structure
H2, Pd/C
EtOH
RT, 45 min, 85% (2 steps)
intermediate structure
MeMgI
Et2O
RT, 4.5 h
intermediate structure
H2SO4
Cyclohexane, H2O
RT, 45 min, 96% (2 steps)
intermediate structure
mCPBA
CHCl3
0 °C to RT, ON, 100%
intermediate structure
NaH
DMSO
60 °C, 5.5 d, 93%
intermediate structure
H2SO4
Cyclohexane, CH2Cl2, H2O
RT, 15 min, 85%
intermediate structure
KOt-Bu, CHBr3
Pentane
0 °C to RT, 2.5 h, 85%
intermediate structure
AgClO4
Acetone, H2O
45 °C, 17 h, 100%
intermediate structure
Na
NH3, MeOH
-33 °C, , 62%
intermediate structure
CrO3.2Pyr
CH2Cl2
RT, 15 min, 100%
intermediate structure
Me2CuLi
Et2O
-20 °C, 40 min, 96%
See the Aldol Addition
intermediate structure
NaBH4, NaOH
MeOH
0 °C to RT, ON, 97%
intermediate structure
MsCl, Et3N
CH2Cl2
-20 to -10 °C, 15 min, 100%
intermediate structure
KOt-Bu
t-BuOH
35 °C, 60 min, 100%
intermediate structure
H2, (Ph3P)3RhCl
PhH, MeOH
RT, 4.5 d, 87%
intermediate structure
MeLi
Et2O
48 °C, 3 h
intermediate structure
SOCl2
Pyr
0 °C, 10 min, 85% (2 steps)
intermediate structure