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Named reactions

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Search synthesis

Hirsutene

Chemical structure of Hirsutene
C15H24
Author Tomas Hudlicky
Publication year 1980
Synthesis type Formal synthesis
Number of steps 10 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
LiBr, HMPA
PhMe
Reflux, 35 min

See the Semi-Pinacol Rearrangement
Chemical structure
VinylMgBr
THF
0 °C to RT, 3 h, 90% (2 steps)

See the Grignard Reaction
Chemical structure
MeC(OMe)3, Hg(OAc)2
EtCO2H
Reflux, 18 h

See the Johnson-Claisen Rearrangement
Chemical structure
KOH
EtOH, H2O
Reflux, 2 h, 82% (2 steps)
Chemical structure
(COCl)2
Hexane(s)
Reflux, 60 min
Chemical structure
CH3CHN2
Et2O
RT, 60 min, 95% (2 steps)
Chemical structure
Cu(acac)2
PhH
Reflux, 12 h, 97%
Chemical structure
PbCO3
0.1 mmHg
580 °C, 66%

Also isolated was the C11 epimer (11 % yield).
Chemical structure
H2, Pd/C
3.5 atm
Hexane(s)
RT, 8 h, 97%
Chemical structure

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Remaining...
70% (1 step)

See: Tetrahedron Lett. 1976, 17, 195.
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