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Synlett 2010(18): 2721-2724  
DOI: 10.1055/s-0030-1259010
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Formal Synthesis of AB3217-A from Anisomycin Using a Directed Benzylic Oxidation

Julie Touega, Christopher R. A. Godfrey*a, Jane E. Wibleyb
a Syngenta Crop Protection Münchwilen AG, WST-820.1.15, Schaffhauserstrasse, 4332 Stein, Switzerland
e-Mail: chris.godfrey@syngenta.com;
b Syngenta Crop Protection Jealott’s Hill International Research Centre, Bracknell, Berkshire, R42 6EY, UK
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Publication History

Received 9 September 2010
Publication Date:
22 October 2010 (online)

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Abstract

A formal synthesis of the insecticidal natural product AB3217-A involving an unusual diastereoselective benzylic oxidation is described.

Key words

natural product - anisomycin - AB3217-A - benzylic oxidation - insecticide

    References and Notes

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7

The hypothesis that the migration of the acetate proceeds via formation of an epoxide was ruled out. If an epoxide was formed and re-opened by the acetate, the stereochemistry of the two hydroxy groups on the pyrrolidine moiety would be inverted, which is not the case as can be observed on the crystal structure of 6 (Figure  [³] ).