Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorTakeshi Matsumoto
Publication year1976
Synthesis typeTotal
Number of steps 16 (linear)
References
Tetrahedron Lett. 1976, 17, 2795. Tetrahedron Lett. 1975, 16, 4377. Tetrahedron Lett. 1974, 15, 1545.
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
See the Aldol Condensation
intermediate structure
C2H4
hν
Hexane(s)
0 °C, 6 h, 75%
intermediate structure
NaOt-Amyl, Ph3P+CH3 Br-
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
H2SO4, CrO3
Acetone, H2O
95%
See the Jones Oxidation
intermediate structure
NaOt-Amyl, Ph3P+CH3 Br-
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%
See the Prilezhaev Reaction
intermediate structure
LiAlH4
THF
intermediate structure
MsCl
Pyr
35 °C, 16 h, 9%
"Also isolated was the endocyclic olefin (61 % yield)."
intermediate structure
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