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Synlett 2010(18): 2721-2724
DOI: 10.1055/s-0030-1259010
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
Weitere Informationen
Received
9 September 2010
Publikationsdatum:
22. Oktober 2010 (online)
Publikationsverlauf
Publikationsdatum:
22. Oktober 2010 (online)
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
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References and Notes
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] ).