Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorLutz Fitjer
Publication year1998
Synthesis typeFormal
Number of steps 10 (linear)
References
Tetrahedron 1998, 54, 10713. Synthesis 1994, 1994, 893.
Part 1 of 1
intermediate structure
LiAlH4
Et2O
85%
intermediate structure
TsCl
Pyr
0-5 °C, ON, 80%
intermediate structure
12-Crown-4, LiI
MeCN
Reflux, 3.5 d, 87%
See the Finkelstein Reaction
intermediate structure
Ph3P
PhMe
Reflux, 16 h, 72%
intermediate structure
Special reagent
KOt-Bu
PhH
50 to 70 °C, 7 h, 65%
See the Wittig Reaction
intermediate structure
TsOH
PhH
RT, 30 min, 79%
intermediate structure
Special reagent
EtAlCl2
DCE
0 °C to RT, 23 h, 50%
intermediate structure
KOH
H2O, MeOH
Reflux, 3 d, 96%
intermediate structure
Pb(OAc)4, Pyr
AcOH, PhH
Reflux, 3 h, 49%
intermediate structure
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Remaining...
93% (1 step)
"See: J. Org. Chem. 1990, 55, 2725."
intermediate structure