Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorTheodore Cohen
Publication year1992
Synthesis typeTotal
Number of steps 9 (linear)
References
J. Org. Chem. 1992, 57, 1968.
Part 1 of 1
intermediate structure
  1. (COCl)2
  2. AlCl3
CH2Cl2
0 °C to RT, 16 h, 60%
intermediate structure + intermediate structure
  1. n-BuLi , HC(SPh)3
  2. s-BuLi
  3. FeCl3
DMF
-78 °C to RT, 10.5 h, 64%
intermediate structure
Ni (Raney)
H2O, THF
RT, 4 h, 93%
intermediate structure
TsOH, (CH2OH)2
Dean-Stark
PhH
reflux, 86%
intermediate structure
Li
NH3
-78 °C, 30 min, 92%
intermediate structure
  1. (CH2NMe2)2 , n-BuLi
  2. Cl2P(O)NMe2
  3. Me2NH
DME
0 °C to RT, 4.5 h
intermediate structure
MeNH2, Li
t-BuOH, THF
-6 °C to RT
intermediate structure
TsOH
Acetone, H2O
reflux, 6 h, 82% (3 steps)
intermediate structure
Ph3P+CH3 Br-, KOt-Bu
PhMe
reflux, 20 min, 96%
See the Wittig Reaction
intermediate structure
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