Synthesis of Longifolene

Structure of Longifolene

C15H24

Principal investigatorAlex G. Fallis
Publication year1990
Synthesis typeTotal
Number of steps 17 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
Pyrrolidine
MeOH
0 °C to RT, 4 h, 86%
intermediate structure
MeLi
THF
-78 to 0 °C, 10 min, 65%
intermediate structure + intermediate structure
Phosgene
PhMe
0 °C
"No yield reported."
intermediate structure
LiAlH4
"No yield reported."
intermediate structure
MnO2
81%
intermediate structure + intermediate structure
i-Pr2NLi, CdCl2
THF
-40 to 0 °C, 2.5 h, 73%
See the Aldol Addition
intermediate structure
BF3.OEt2
MeOH
RT, 4 h, 83%
intermediate structure
PhMe
2.5 h, 97%
intermediate structure
H2, Pd/C
EtOAc
RT, 4 h, 99%
intermediate structure
LiAlH4
Et2O
0 °C to RT, 4 h, 95%
intermediate structure
Ac2O, Pyr
Et2O
0 °C, 6 h, 74%
intermediate structure
PhOC(S)Cl, Pyr
CH2Cl2
RT
intermediate structure
n-Bu3SnH, AIBN
PhMe
110 °C, 4 h, 71%
intermediate structure
NaI, TMSCl, Et3N
CH2Cl2
RT, 60 min
intermediate structure
PhOC(S)Cl, Pyr
CH2Cl2
RT
intermediate structure
n-Bu3SnH, AIBN
PhMe
110 °C, 4 h, 50% (3 steps)
intermediate structure
PhH
525 °C, , 56%
intermediate structure