Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorBenjamin List
Publication year2008
Synthesis typeTotal
Number of steps 12 (linear)
References
Part 1 of 1
intermediate structure
(COCl)2, Et3N, DMSO
CH2Cl2
-78 to 0 °C, 2.5 h
See the Swern Oxidation
intermediate structure
Special reagent
CH2Cl2
0 °C, 3 h, 76% (2 steps)
See the Wittig Reaction
intermediate structure
Mg
MeOH
0 °C, 3.5 h, 88%
intermediate structure
KOH
EtOH, H2O
0 °C to RT, 24 h, 77%
intermediate structure
(COCl)2
CH2Cl2, DMF
0 °C
intermediate structure
TMSCHN2
MeCN, THF
0 °C, 4 h, 73%
intermediate structure
(Ph3P)CpRuCl
CH2Cl2
55 °C, 30 min, 52%
"Also isolated was 22% trans isomer"
intermediate structure
Pd/C, H2
1 atm
EtOAc
RT, 3 h, 91%
intermediate structure
Special reagent
DMSO
RT, 24 h, 84%
See the Aldol Addition
"95% ee"
intermediate structure
NaOH
Et2O, H2O
RT, 24 h, 99%
intermediate structure
  1. Li
  2. MeI
NH3, THF
-78 °C, 20 min, 75%
intermediate structure
KOt-Bu, Ph3P+CH3 Br-
PhMe
0 °C to reflux, 3 h, 87%
See the Wittig Reaction
intermediate structure