An Asymmetric Synthesis of (+)-Grandisol, a Constituent of the Aggregation Pheromone of the Cotton Boll Weevil, via a Kinetic Resolution

A novel approach to the asymmetric synthesis of (+)-grandisol, (1R,2S)-isopropenyl-1-methylcyclobutaneethanol, involves the use of catalytic kinetic resolution of a primary allylic alcohol, [(1RS,5SR)-5-methylbicyclo[3.2.0]hept-2-en-2-yl] methanol. The allylic alcohol is prepared in four steps from...

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Bibliographic Details
Published in:Journal of organic chemistry 2000-11, Vol.65 (23), p.7839-7846
Main Authors: Hamon, David P. G, Tuck, Kellie L
Format: Article
Language:English
Subjects:
Pheromones - chemical synthesis
Stereoisomerism
Terpenes - chemical synthesis
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Summary:A novel approach to the asymmetric synthesis of (+)-grandisol, (1R,2S)-isopropenyl-1-methylcyclobutaneethanol, involves the use of catalytic kinetic resolution of a primary allylic alcohol, [(1RS,5SR)-5-methylbicyclo[3.2.0]hept-2-en-2-yl] methanol. The allylic alcohol is prepared in four steps from simple achiral materials involving the use of a modified Shapiro reaction. The resolved alcohol (95% ee) is then reduced in two steps to the corresponding methyl alkene, (1S,5R)-2,5-dimethylbicyclo[3.2.0]hept-2-ene. This alkene is converted to (+)-grandisol (95% ee), in three steps, by modified literature procedures.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo000853+