Syntheses of Papyracillic Acids: Application of the Tandem Chain Extension-Acylation Reaction

Abstract

A synthetic approach to the papyracillic acid family of natural products has been developed. The spiroacetal core is rapidly assembled through an unprecedented zinc carbenoid-mediated tandem chain extension–acylation reaction. Subsequent functional group manipulation provided access to papyracillic acid B and 4-epi-papyracillic acid C. The successful preparation of these molecules resulted in the clarification of structural assignments of members of this family of natural products.

Department

Chemistry

Publication Date

10-19-2012

Journal Title

Journal of Organic Chemistry

Publisher

American Chemical Society

Digital Object Identifier (DOI)

10.1021/jo3017617

Document Type

Article

Rights

Copyright © 2012, American Chemical Society

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