Synthesis of Hirsutene

C15H24
Principal investigator | R. Daniel Little |
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Publication year | 1983 |
Synthesis type | Formal |
Number of steps | 16 (linear) |
References |
Part 1 of 1
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NaBH4
THF
0 °C to RT, 3.5 h, 61%

i-Bu2AlH
Et2O
-20 °C, 90 min, 76%


HCrO3Cl.Pyr,
Celite
CH2Cl2
"No yield reported."


Et2NH
MeOH
5 °C to RT, 2 h, 77%




AcOH
CH2Cl2
"No yield reported."

LiClO4,
K3Fe(CN)6
-1.76 V vs Ag/AgCl
DMF, H2O
0 °C to RT, 2 h, 55%

THF
Reflux, 6 h, 63%
"Also isolated was the C6-epimer (13 % yield)."

BH3.THF
THF

Celite,
HCrO3Cl.Pyr
CH2Cl2
61% (2 steps)


TsOH,
MgSO4,
n-BuSH
PhH
Reflux, 20 h, 82%

KOt-Bu,
MeI
t-BuOH
0 °C to reflux, 30 min, 50%
"The yield was 59% BRSM."

KOH
Ethylene Glycol, H2O
Reflux, 24 h, 51%

Remaining...
70% (1 step)
"See: Tetrahedron Lett. 1976, 17, 195."
