Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorSteven V. Ley
Publication year1982
Synthesis typeTotal
Number of steps 12 (3 parts)
References
Part 1 of 3
intermediate structure
KOt-Bu, n-BuLi
HMPA, THF
-78 °C, 80 min
intermediate structure
LiAlH4
Et2O
0 °C to RT, 60 min, 86% (2 steps)
intermediate structure
Br2, Ph3P
DMF, PhH
RT, 4 h, 59%
See the Appel Reaction
intermediate structure
Part 2 of 3
intermediate structure
PhSeCl
Pyr
0 °C to RT, 105 min, 100%
intermediate structure
H2O2
CH2Cl2, H2O
0 °C to RT, 60 min, 96%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
CuBr.Me2S, Mg
THF
-50 °C to RT, 80 min, 58%
intermediate structure
SnCl4, N-(Phenylselenyl)phthalimide
CH2Cl2
0 °C to RT, 2.5 h, 45%
intermediate structure
Ni (Raney)
EtOH
50 °C, 2 h, 91%
intermediate structure
i-Pr2NLi, LiAlH4
THF
-78 to -20 °C, 2.5 h, 66%
intermediate structure
n-Bu3P, N-(Phenylselenyl)phthalimide
THF
RT, 2 h, 62%
intermediate structure
Ni (Raney)
EtOH
45 °C, 20 min, 83%
intermediate structure
TiCl4, Zn, CH2Br2
CH2Cl2, THF
-40 to 0 °C, 20 h, 98%
intermediate structure