Synthesis of Hirsutene

C15H24
Principal investigator | Wolfgang Oppolzer |
---|---|
Publication year | 1994 |
Synthesis type | Total |
Number of steps | 19 (linear) |
References |
Part 1 of 1
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HCrO3Cl.Pyr,
Celite
CH2Cl2
RT, 90 min, 89%


i-Bu2AlH
CH2Cl2
-78 °C, 3 h, 97%


Pyr,
ClCO2Me
CH2Cl2
RT, 1.5 h, 92%


CH2N2
Et2O
RT, 61% (2 steps)

Pd/C,
H2
1 atm
EtOH
RT, 3 h, 100%

NaBH4
EtOH
-18 °C, 30 min, 97%

POCl3
Pyr
-17 to 35 °C, 3 d, 82%


LDA
THF
-78 to °C, 3 d

H2SO4
Dioxane
RT, 20 h, 40% (48% BRSM)
"57:43 @ C-1"

NaBH4,
(PhSe)2
DMF
80 to 120 °C, 2 h

CH2N2
Et2O
RT, 68% (2 steps)
"54:46 @ C-1"

AIBN,
n-Bu3SnH
PhMe
Reflux, 20 h, 92%
"53:47 @ C-11"

LiAlH4
Et2O
RT, 2 h, 89%
"80:20 @ C-11"

n-Bu3P,
o-NO2PhSeCN
THF
RT, 16 h, 87%

