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

Abstract

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

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

References and Notes

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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] ).

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