Synthesis of Longifolene

Structure of Longifolene

C15H24

Principal investigatorArthur G. Schultz
Publication year1985
Synthesis typeFormal
Number of steps 14 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
K
NH3, THF, t-BuOH
-78 °C, , 98%
See the Birch Reduction
intermediate structure
HCl
MeOH
intermediate structure
ClCO2Me, NaHCO3
intermediate structure
HCl, HC(OMe)3
MeOH
Reflux
intermediate structure
NaOMe
MeOH
75% (4 steps)
intermediate structure
NBS
MeOH
95%
intermediate structure
DBU
PhMe
Reflux, , 85%
intermediate structure
TsOH
Acetone
Reflux, , 86%
intermediate structure + intermediate structure
intermediate structure
Xylene(s)
Reflux, , 40% (2 steps)
intermediate structure
H2, Pd/C
EtOH
RT, , 92%
intermediate structure
KOH
MeOH, H2O
RT, , 85%
intermediate structure
PhMe
Reflux, , 86%
intermediate structure
Remaining...
75% (3 steps)
"See : J. Am. Chem. Soc. 1978, 100, 2583."
intermediate structure