Synthesis of Longifolene
C15H24
| Principal investigator | Elias J. Corey |
|---|---|
| Publication year | 1961 |
| Synthesis type | Total |
| Number of steps | 14 (linear) |
| References |
Part 1 of 1
+
(CH2OH)2,
TsOH
Dean-Stark
PhH
Reflux, 66%
+
OsO4,
Pyr
Et2O
-20 °C to RT, 26 h
Pyr,
TsCl
CH2Cl2
0 °C, 23 h
CaCO3,
LiClO4
THF
50 °C, 2.5 d, 48% (3 steps)
HCl
EtOH, H2O
RT, 4 h, 100%
Et3N
Sealed tube
Ethylene Glycol
225 °C, 24 h, 8-12%
See the Michael Addition
"The yield was 10-15 % brsm."
- Ph3CNa
- MeI
Dioxane , Et2O
30 °C, 36 h, 59%
BF3.OEt2,
(CH2SH)2
RT, 90 min, 72%
LiAlH4
Et2O
Reflux, 5 h, 100%
CrO3,
MnSO4
AcOH, H2O
RT to 55 °C, 90 min, 82%
MeLi
Et2O
Reflux, 3 d, 93%
Pyr,
SOCl2
CFCl3
0 °C, 12 min, 95%