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Named reactions

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Search synthesis

Laurenene

Chemical structure of Laurenene
C20H32
Author Leo A. Paquette
Publication year 1988
Synthesis type Formal synthesis
Number of steps 24 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
CuBr.Me2S
THF, Me2S
-78 to 0 °C, 6 h

See the Michael Addition
Chemical structure
HCl
Acetone, H2O
RT, 3 d, 79% (2 steps)

See the Aldol Addition
Chemical structure
MsCl, Et3N
CH2Cl2
0 °C, 30 min
Chemical structure
DBU
CH2Cl2
RT, ON, 76% (2 steps)
Chemical structure
MeLi
Et2O
-78 °C to RT, ON
Chemical structure
HCrO3Cl.Pyr, Celite ®
CH2Cl2
RT, ON, 70% (2 steps)
Chemical structure + Chemical structure
CuBr.Me2S
THF, Me2S
-78 to 0 °C, 68%

See the Michael Addition
Chemical structure
HCl
THF, H2O
RT, 71%

See the Aldol Addition
Chemical structure
ClC(S)O(p-MePh), Pyr
THF
RT, ON, 84%
Chemical structure
200 °C, 100%

See the Chugaev Elimination
Chemical structure
TMSCN, ZnI2
PhH
RT, 18 h, 96%
Chemical structure
POCl3, DBU
Pyr
Reflux, 20 h, 92%
Chemical structure
Mg
MeOH
RT, 11 h, 95%
Chemical structure + Chemical structure
i-Pr2NLi, HMPA
THF
-78 °C to RT, 6 h, 83%
Chemical structure
i-Bu2AlH
PhH
RT, 60 min
Chemical structure
NH2NH2, K2CO3
Diethylene glycol
260 °C, 19 h, 63% (2 steps)

See the Wolff-Kishner Reduction
Chemical structure
  1. BH3.Me2S
  2. H2O2, H2O
THF
0 to 50 °C, 43 h
Chemical structure
+
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 22 min, 62% (2 steps)

See the Swern Oxidation
Also isolated was the C4-ketone (10 % yield).
Chemical structure
TsOH
PhH
Reflux, 4 h, 78%

See the Claisen-Schmidt Condensation
Chemical structure

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Remaining...
9% (5 steps)

See : J. Am. Chem. Soc. 1987, 109, 6199.
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