Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorTomas Hudlicky
Publication year1980
Synthesis typeFormal
Number of steps 10 (linear)
References
Part 1 of 1
intermediate structure
LiBr, HMPA
PhMe
Reflux, 35 min
intermediate structure
VinylMgBr
THF
0 °C to RT, 3 h, 90% (2 steps)
intermediate structure
MeC(OMe)3, Hg(OAc)2
EtCO2H
Reflux, 18 h
intermediate structure
KOH
EtOH, H2O
Reflux, 2 h, 82% (2 steps)
intermediate structure
(COCl)2
Hexane(s)
Reflux, 60 min
intermediate structure
CH3CHN2
Et2O
RT, 60 min, 95% (2 steps)
intermediate structure
Cu(acac)2
PhH
Reflux, 12 h, 97%
intermediate structure
PbCO3
580 °C, , 66%
"Also isolated was the C11 epimer (11 % yield)."
intermediate structure
H2, Pd/C
Hexane(s)
RT, 8 h, 97%
intermediate structure
Remaining...
70% (1 step)
"See: <i>Tetrahedron Lett. 1976, 17, 195."
intermediate structure