Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorDennis P. Curran
Publication year1985
Synthesis typeTotal
Number of steps 12 (linear)
References
Part 1 of 1
intermediate structure
  1. i-Pr2NLi
  2. TBSCl
HMPA, THF
-78 °C, 90 min
intermediate structure
CHCl3
Reflux, 5 h
intermediate structure
PhSeCl
CH2Cl2
-78 °C, 25 min, 75% (3 steps)
intermediate structure
H2O2
H2O, THF
0 °C, ON, 82%
intermediate structure + intermediate structure
CuBr.Me2S, Li.Naphthalene
THF, Me2S
-78 to -20 °C, 5.5 h
intermediate structure
Pyr.TsOH
EtOH
Reflux, 4 h, 75% (2 steps)
intermediate structure
i-Bu2AlH
THF
-78 °C to RT, 7 h, 83%
intermediate structure
Pyr, Tf2O
CH2Cl2
-10 °C, 70 min, 81%
intermediate structure
n-Bu4N+ I-
PhH
Reflux, 2 h, 75%
intermediate structure
n-BuLi, Trimethylsilylacetylene
HMPA, THF
0 °C, 20 min
intermediate structure
n-Bu4N+ F-
THF
RT, 2 h, 75% (2 steps)
intermediate structure
AIBN, n-Bu3SnH
PhH
Reflux, 60 min, 64%
intermediate structure