Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorMichel Franck-Neumann
Publication year1989
Synthesis typeFormal
Number of steps 10 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
CuBr.Me2S
THF
-78 °C, 15 h
intermediate structure
HCl
THF, H2O
40 °C, 24 h, 84% (2 steps)
See the Aldol Addition
intermediate structure
BzCl
Pyr
RT, 4 h, 90%
intermediate structure
TsOH, Morpholine
PhEt
Reflux, 24 h, 91%
intermediate structure + intermediate structure
Et2O
RT, 24 h, 40%
intermediate structure
HI
PhMe, H2O
RT, 4 h, 85%
intermediate structure
H2, Pd/C, Et3N
MeOH
RT, 12 h, 91%
intermediate structure
Li
NH3
30%
intermediate structure
HCrO3Cl.Pyr
CH2Cl2
RT, 30 min, 100%
intermediate structure
Remaining...
98% (1 step)
"See: Tetrahedron 1985, 41, 4765."
intermediate structure