Synthesis of Hirsutene

C15H24
Principal investigator | Steven V. Ley |
---|---|
Publication year | 1982 |
Synthesis type | Total |
Number of steps | 12 (3 parts) |
References |
Part 1 of 3

KOt-Bu,
n-BuLi
HMPA, THF
-78 °C, 80 min

LiAlH4
Et2O
0 °C to RT, 60 min, 86% (2 steps)


Part 2 of 3

PhSeCl
Pyr
0 °C to RT, 105 min, 100%

H2O2
CH2Cl2, H2O
0 °C to RT, 60 min, 96%

Part 3 of 3
+



N-(Phenylselenyl)phthalimide,
SnCl4
CH2Cl2
0 °C to RT, 2.5 h, 45%

Ni (Raney)
EtOH
50 °C, 2 h, 91%

LiAlH4,
i-Pr2NLi
THF
-78 to -20 °C, 2.5 h, 66%

N-(Phenylselenyl)phthalimide,
n-Bu3P
THF
RT, 2 h, 62%

Ni (Raney)
EtOH
45 °C, 20 min, 83%

