Synthesis of Hirsutene

C15H24
Principal investigator | Takeshi Matsumoto |
---|---|
Publication year | 1976 |
Synthesis type | Total |
Number of steps | 16 (linear) |
References |
Part 1 of 1

NaCN
DMSO
80 °C, 6 h

KOH
H2O
Reflux, 18 h

MeLi
Et2O


C2H4
hν
Hexane(s)
0 °C, 6 h, 75%


Tl(ClO4)3
H2O, t-BuOH
RT, 24 h, 57%

NaBH4
EtOH
0 °C, 2 h, 100%

TsOH
PhH
80 °C, 2 h, 70%

LiAlH4
THF
RT, 15 h, 97%
"R = H, Ts"



TsOH
PhH
80 °C, 20 min, 95%


LiAlH4
THF

MsCl
Pyr
35 °C, 16 h, 9%
"Also isolated was the endocyclic olefin (61 % yield)."
