期刊
TETRAHEDRON LETTERS
卷 51, 期 51, 页码 6704-6706出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.10.024
关键词
Hedyphates betulinus; Sex pheromone; Kinetic resolution; Absolute configuration
资金
- Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq, Brazil)
- Instituto Nacional de Ciencias e Tecnologia de Semioquimicos na Agricultura
The male-produced sex pheromone of Hedypathes betulinus was identified as a mixture of (E)-6,10-dimethyl-5,9-undecadien-2-one (geranylacetone) (1) and its respective alcohol (2) and acetate (3). Kinetic resolution of alcohol (2) promoted by CAL-B in organic media provided both, (R)-(-)-(E)-6,10-dimethy1-5,9-undecadien-2-yl acetate (3) and (S)-(+)-(E)-6,10-dimethyl-5,9-undecadien-2-ol (2) in high enantiomeric purity. Comparative GC analysis using a chiral column revealed the natural constituents as being (R)-(3) and a mixture of (R)- and (S)-(2) in a ratio of 82.3% and 17.6%, respectively. (C) 2010 Elsevier Ltd. All rights reserved.
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