Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorWolfgang Oppolzer
Publication year1994
Synthesis typeTotal
Number of steps 19 (linear)
References
Tetrehedron 1994, 50, 415.
Part 1 of 1
intermediate structure + intermediate structure
CH2Cl2
Reflux, 4 d, 97%
See the Wittig Reaction
"93:07 E/Z"
intermediate structure
HCrO3Cl.Pyr, Celite
CH2Cl2
RT, 90 min, 89%
intermediate structure
Zn, CBr4, PPh3
CH2Cl2
RT, 1 h, 100%
See the Corey-Fuchs Reaction
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C, 3 h, 97%
intermediate structure
n-BuLi
THF
-78 to 0 °C, 4.3 h, 85%
See the Corey-Fuchs Reaction
intermediate structure
Pyr, ClCO2Me
CH2Cl2
RT, 1.5 h, 92%
intermediate structure
CO, PPh3, Pd(dba)2
AcOH
40 °C, 21 h
See the Pauson-Khand Reaction
intermediate structure
CH2N2
Et2O
RT, 61% (2 steps)
intermediate structure
Pd/C, H2
1 atm
EtOH
RT, 3 h, 100%
intermediate structure
NaBH4
EtOH
-18 °C, 30 min, 97%
intermediate structure
POCl3
Pyr
-17 to 35 °C, 3 d, 82%
intermediate structure
Special reagent
LDA
THF
-78 to °C, 3 d
intermediate structure
H2SO4
Dioxane
RT, 20 h, 40% (48% BRSM)
"57:43 @ C-1"
intermediate structure
NaBH4, (PhSe)2
DMF
80 to 120 °C, 2 h
intermediate structure
CH2N2
Et2O
RT, 68% (2 steps)
"54:46 @ C-1"
intermediate structure
AIBN, n-Bu3SnH
PhMe
Reflux, 20 h, 92%
"53:47 @ C-11"
intermediate structure
LiAlH4
Et2O
RT, 2 h, 89%
"80:20 @ C-11"
intermediate structure
n-Bu3P, o-NO2PhSeCN
THF
RT, 16 h, 87%
intermediate structure
H2O2
H2O, THF
0 to 50 °C, 75 min, 90%
See the Grieco Dehydration
intermediate structure
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