Synthesis of Longifolene

C15H24
Principal investigator | John E. McMurry |
---|---|
Publication year | 1972 |
Synthesis type | Total |
Number of steps | 18 (linear) |
References |
Part 1 of 1

(CH2OH)2,
TsOH
Dean-Stark
PhH
Reflux, 25 min

H2,
Pd/C
1 atm
EtOH
RT, 45 min, 85% (2 steps)


H2SO4
Cyclohexane, H2O
RT, 45 min, 96% (2 steps)


NaH
DMSO
60 °C, 5.5 d, 93%

H2SO4
Cyclohexane, CH2Cl2, H2O
RT, 15 min, 85%

KOt-Bu,
CHBr3
Pentane
0 °C to RT, 2.5 h, 85%

AgClO4
Acetone, H2O
45 °C, 17 h, 100%

Na
MeOH, NH3
-33 °C, 62%



NaBH4,
NaOH
MeOH
0 °C to RT, ON, 97%

Et3N,
MsCl
CH2Cl2
-20 to -10 °C, 15 min, 100%


H2,
(Ph3P)3RhCl
1 atm
MeOH, PhH
RT, 4.5 d, 87%

MeLi
Et2O
48 °C, 3 h

SOCl2
Pyr
0 °C, 10 min, 85% (2 steps)
