Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorDaniel D. Sternbach
Publication year1990
Synthesis typeTotal
Number of steps 22 (linear)
References
Part 1 of 1
intermediate structure
TsOH, HC(OEt)3
EtOH
Reflux, 6 h, 95%
intermediate structure
  1. O3
  2. Ph3P
CH2Cl2
-78 °C to RT, ON, 100%
intermediate structure + intermediate structure
PhH
RT to Reflux, 6 h, 81%
See the Wittig Reaction
intermediate structure
LiAlH4
Et2O
0 °C, 6 h, 99%
intermediate structure
HCl
H2O, THF
RT, 25 min, 100%
intermediate structure + intermediate structure
Na2S2O4, Pyrrolidine
MeOH
RT, 24-36 h, 99%
intermediate structure
LiAlH4
THF
RT, 6 h, 93%
intermediate structure
Mesitylene
Reflux, 24 h, 70%
intermediate structure
CrO3, H2SO4
Acetone, H2O
0 °C, 60 min, 97%
See the Jones Oxidation
intermediate structure
  1. Me2S
  2. O3
CH2Cl2
-78 °C to RT, , 99%
intermediate structure
Ac2O, DMAP, Et3N
CH2Cl2
RT, 4 h, 90%
intermediate structure
CrO3, H2SO4
Acetone, H2O
RT, 45 min, 95%
See the Jones Oxidation
intermediate structure
(COCl)2, DMF
PhH
RT, 2 h
intermediate structure
DMAP, t-BuSH
PhMe
Reflux, 45 min, 82% (2 steps)
intermediate structure
Et3N
H2O, MeOH
RT, 60 min, 95%
intermediate structure
TMS2NK, Ph3P+CH3 Br-
THF
0 °C to RT, 30 min, 86%
See the Wittig Reaction
intermediate structure
(COCl)2, NaH
PhH
RT, 4 h
intermediate structure
Me2CuLi
Et2O
-78 to 0 °C, 60 min, 97% (2 steps)
intermediate structure
  1. Me2S
  2. O3
CH2Cl2
-78 °C to RT, , 80%
intermediate structure
KOH, n-Bu4N+ OH-
Et2O, THF
Reflux, ON, 97%
intermediate structure
H2, PtO2
EtOAc
RT, 20 min, 100%
intermediate structure
KH, Ph3P+CH3 Br-
PhH, t-BuOH
RT to Reflux, 6 h, 93%
See the Wittig Reaction
intermediate structure