Synthesis of Longifolene

Structure of Longifolene

C15H24

Principal investigatorJohn E. McMurry
Publication year1972
Synthesis typeTotal
Number of steps 18 (linear)
References
J. Am. Chem. Soc. 1972, 94, 7132.
Part 1 of 1
intermediate structure
(CH2OH)2, TsOH
Dean-Stark
PhH
Reflux, 25 min
intermediate structure
H2, Pd/C
1 atm
EtOH
RT, 45 min, 85% (2 steps)
intermediate structure
MeMgI
Et2O
RT, 4.5 h
See the Grignard Reaction
intermediate structure
H2SO4
Cyclohexane, H2O
RT, 45 min, 96% (2 steps)
intermediate structure
mCPBA
CHCl3
0 °C to RT, ON, 100%
See the Prilezhaev Reaction
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
MeOH, NH3
-33 °C, 62%
intermediate structure
CrO3.2Pyr
CH2Cl2
RT, 15 min, 100%
See the Sarett Oxidation
intermediate structure
Me2CuLi
Et2O
-20 °C, 40 min, 96%
See the Aldol Addition
See the Michael Addition
intermediate structure
NaBH4, NaOH
MeOH
0 °C to RT, ON, 97%
intermediate structure
Et3N, MsCl
CH2Cl2
-20 to -10 °C, 15 min, 100%
intermediate structure
KOt-Bu
t-BuOH
35 °C, 60 min, 100%
See the Grob Fragmentation
intermediate structure
H2, (Ph3P)3RhCl
1 atm
MeOH, PhH
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
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