Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorDuy H. Hua
Publication year1985
Synthesis typeTotal
Number of steps 16 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
  1. AcCl
  2. i-Pr2NLi
HMPA, THF
-78 °C, 105 min, 86%
intermediate structure
Zn
AcOH
RT, 10 h, 95%
intermediate structure
TiCl4
AcOH
RT, 20 min, 86%
intermediate structure
(CH2OH)2, TsOH
PhH
Reflux, 6 h, 95%
intermediate structure
mCPBA
CH2Cl2
-20 to 0 °C, 5 h, 95%
intermediate structure
DBN
PhMe
Reflux, 10 h, 90%
intermediate structure
CrO3.2Pyr
CH2Cl2
RT, 24 h, 85%
intermediate structure + intermediate structure
Li, CuI.Me2S
Et2O
-30 °C to RT, 2.5 h, 85%
"Also isolated was the C6'-epimer (5 % yield)."
intermediate structure
n-Bu4N+ F-
THF
RT, 15 h, 97%
intermediate structure
TsCl
Pyr
RT, 20 h, 99%
intermediate structure
NaH
DME
Reflux, 5 h, 90%
intermediate structure
NaBH4
MeOH
-10 °C, 60 min, 95%
intermediate structure
Et3N, i-PrSO2Cl
Et2O
0 °C to RT, 3 h, 93%
intermediate structure
LiBHEt3
PhMe
90 °C, 24 h, 72%
intermediate structure
TsOH
H2O, MeOH, THF
RT, 60 min, 90%
intermediate structure
Ph3P+CH3 Br-, NaOt-Amyl
PhMe
RT to reflux, 4 h, 80%
See the Wittig Reaction
intermediate structure