Stereoselective synthesis of hydroxylated bifenthrin isomers

Two isomeric, hydroxylated derivatives of the potent insecticide/acaricide bifenthrin were prepared from a common precursor. A high degree of control over the relative stereochemistry at all three stereogenic centers was achieved by closure of the C1-C3 bond of the cyclopropane ring using a judiciou...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 1992-12, Vol.2 (12), p.1585-1588
Main Authors: Sieburth, Scott McN, Ali, Syed F., Langevine, Charles M., Tullman, Robert H.
Format: Article
Language:English
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Summary:Two isomeric, hydroxylated derivatives of the potent insecticide/acaricide bifenthrin were prepared from a common precursor. A high degree of control over the relative stereochemistry at all three stereogenic centers was achieved by closure of the C1-C3 bond of the cyclopropane ring using a judicious choice of ring closure substrates. Two possible metabolites of bifenthrin, a potent insecticide/acaricide, were prepared from 4-methyl-4-vinylcyclobutanone with substantial control of stereochemistry.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(00)80435-7