Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorGoverdhan Mehta
Publication year1981
Synthesis typeTotal
Number of steps 10 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
PhH
Reflux, 2 h, 90%
intermediate structure
EtOAc
30 min, 85%
intermediate structure
500 °C, , 100%
intermediate structure
BnOBz
317 °C, 12 min, 37%
"The yield was 43 % brsm."
intermediate structure
H2, Pd/C
EtOAc
RT, 20 min, 95%
intermediate structure
MeI, NaH
THF
10 °C to Reflux, 60 min, 65%
intermediate structure
Ph3P+CH3 Br-, NaOt-Amyl
PhMe
RT to Reflux, 3 h, 84%
See the Wittig Reaction
intermediate structure
LiAlH4
Et2O
RT, 45 min, 90%
intermediate structure
  1. NaH
  2. Imidazole
  3. CS2
  4. MeI
THF
Reflux, 4.5 h, 88%
intermediate structure
n-Bu3SnH
PhMe
Reflux, 6 h, 19%
intermediate structure