Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorTakeshi Matsumoto
Publication year1976
Synthesis typeTotal
Number of steps 16 (linear)
References
Part 1 of 1
intermediate structure
NaCN
DMSO
80 °C, 6 h
intermediate structure
KOH
H2O
Reflux, 18 h
intermediate structure
MeLi
Et2O
intermediate structure
KOt-Bu
t-BuOH
0 °C, 60 min
intermediate structure
C2H4
Hexane(s)
0 °C, 6 h, 75%
intermediate structure
Ph3P+CH3 Br-, NaOt-Amyl
PhH
80 °C, 60 min, 92%
See the Wittig Reaction
intermediate structure
Tl(ClO4)3
H2O, t-BuOH
RT, 24 h, 57%
intermediate structure
NaBH4
EtOH
0 °C, 2 h, 100%
intermediate structure
TsOH
PhH
80 °C, 2 h, 70%
intermediate structure
LiAlH4
THF
RT, 15 h, 97%
"R = H, Ts"
intermediate structure
CrO3, H2SO4
Acetone, H2O
95%
See the Jones Oxidation
intermediate structure
Ph3P+CH3 Br-, NaOt-Amyl
PhH
RT, 2 h, 92%
See the Wittig Reaction
intermediate structure
TsOH
PhH
80 °C, 20 min, 95%
intermediate structure
mCPBA
CH2Cl2
RT, 30 min, 98%
intermediate structure
LiAlH4
THF
intermediate structure
MsCl
Pyr
35 °C, 16 h, 9%
"Also isolated was the endocyclic olefin (61 % yield)."
intermediate structure