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Named reactions

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Search synthesis

Hirsutene

Chemical structure of Hirsutene
C15H24
Author Takeshi Matsumoto
Publication year 1976
Synthesis type Total synthesis
Number of steps 16 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
NaCN
DMSO
80 °C, 6 h
Chemical structure
KOH
H2O
Reflux, 18 h
Chemical structure
MeLi
Et2O
Chemical structure
KOt-Bu
t-BuOH
0 °C, 60 min

See the Aldol Condensation
Chemical structure
C2H4
Hexane(s)
0 °C, 6 h, 75%
Chemical structure
Ph3P+CH3 Br-, NaOt-Amyl
PhH
80 °C, 60 min, 92%

See the Wittig Reaction
Chemical structure
Tl(ClO4)3
t-BuOH, H2O
RT, 24 h, 57%
Chemical structure
NaBH4
EtOH
0 °C, 2 h, 100%
Chemical structure
TsOH
PhH
80 °C, 2 h, 70%
Chemical structure
LiAlH4
THF
RT, 15 h, 97%

R = H, Ts
Chemical structure
CrO3, H2SO4
Acetone, H2O
95%

See the Jones Oxidation
Chemical structure
Ph3P+CH3 Br-, NaOt-Amyl
PhH
RT, 2 h, 92%

See the Wittig Reaction
Chemical structure
TsOH
PhH
80 °C, 20 min, 95%
Chemical structure
mCPBA
CH2Cl2
RT, 30 min, 98%

See the Prilezhaev Reaction
Chemical structure
LiAlH4
THF
Chemical structure
MsCl
Pyr
35 °C, 16 h, 9%

Also isolated was the endocyclic olefin (61 % yield).
Chemical structure

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