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Named reactions

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Search synthesis

Capnellene

Chemical structure of Capnellene
C15H24
Author Leo A. Paquette
Publication year 1984
Synthesis type Total synthesis
Number of steps 12 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
LiBr, HMPA
PhMe
Reflux, 2 h

See the Semi-Pinacol Rearrangement
Chemical structure
+
Chemical structure
VinylMgBr
THF
10 °C to RT, 4.5 h, 46% (2 steps)

See the Grignard Reaction
Chemical structure
MnO2/C
Petroleum ether
RT, 24 h, 95%
Chemical structure
P2O5
MsOH
0 °C, 2 min, 68%

See the Nazarov Cyclization Reaction
Chemical structure
MeLi.LiBr, CuI
Et2O
0 °C, 30 min, 80%

See the Michael Addition
Chemical structure
C2H2, n-BuLi
THF
-78 to -20 °C, 15 min, 71%

The yield was 78 & brsm.
Chemical structure
H2SO4
HCO2H
92 °C, 15 min, 89%

See the Rupe Rearrangement
Chemical structure
VinylMgBr, CuI
THF
-78 °C to RT, 30 min, 55%

See the Michael Addition
Chemical structure
  1. O3
  2. Me2S
MeOH
-78 °C to RT, 35 min
Chemical structure
n-Bu4N+ OH-, KOH
THF, Et2O, H2O
Reflux, 4 h, 84% (2 steps)

See the Aldol Condensation
Chemical structure
H2, PtO2
1 atm
MeOH
RT
Chemical structure
Ph3P+CH3 Br-, KOt-Bu
PhH
RT to Reflux, 21.5 h, 36% (2 steps)

See the Wittig Reaction
Chemical structure

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