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Named reactions

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Search synthesis

Hirsutene

Chemical structure of Hirsutene
C15H24
Author Duy H. Hua
Publication year 1985
Synthesis type Total synthesis
Number of steps 16 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
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Chemical structure
  1. i-Pr2NLi
  2. AcCl
THF, HMPA
-78 °C, 105 min, 86%

See the Michael Addition
Chemical structure
Zn
AcOH
RT, 10 h, 95%
Chemical structure
TiCl4
AcOH
RT, 20 min, 86%

Selectivity : 20:80 α/β
Chemical structure
(CH2OH)2, TsOH
Dean-Stark
PhH
Reflux, 6 h, 95%
Chemical structure
mCPBA
CH2Cl2
-20 to 0 °C, 5 h, 95%
Chemical structure
DBN
PhMe
Reflux, 10 h, 90%
Chemical structure
CrO3.2Pyr
CH2Cl2
RT, 24 h, 85%
Chemical structure + Chemical structure
Li, CuI.Me2S
Et2O
-30 °C to RT, 2.5 h, 85%

See the Michael Addition
Also isolated was the C6'-epimer (5 % yield).
Chemical structure
n-Bu4N+ F-
THF
RT, 15 h, 97%
Chemical structure
TsCl
Pyr
RT, 20 h, 99%
Chemical structure
NaH
DME
Reflux, 5 h, 90%
Chemical structure
NaBH4
MeOH
-10 °C, 60 min, 95%
Chemical structure
i-PrSO2Cl, Et3N
Et2O
0 °C to RT, 3 h, 93%
Chemical structure
LiBHEt3
PhMe
90 °C, 24 h, 72%
Chemical structure
TsOH
THF, MeOH, H2O
RT, 60 min, 90%
Chemical structure
Ph3P+CH3 Br-, NaOt-Amyl
PhMe
RT to reflux, 4 h, 80%

See the Wittig Reaction
Chemical structure

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