Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorAlan C. Weedon
Publication year1987
Synthesis typeFormal
Number of steps 7 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
MeOH
RT, 5 d
intermediate structure + intermediate structure
TBSCl, Imidazole
DMF, CH2Cl2
0 °C to RT, 2 h, 89%
intermediate structure + intermediate structure
TiCl3, K
THF
Reflux, 25 h, 55%
intermediate structure + intermediate structure
n-Bu4N+ F-
THF
RT, 12 h, 52%
intermediate structure
H2, PtO2
MeOH
RT, 10 h
intermediate structure
CrO3, H2SO4
Acetone, H2O
0 °C, , 47% (2 steps)
See the Jones Oxidation
intermediate structure
Remaining...
70% (1 step)
"Tetrahedron Lett. 1976, 17, 195."
intermediate structure