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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.

SUBMITTER: Mazzone JR

PROVIDER: S-EPMC3477294 | biostudies-literature | 2012 Oct

REPOSITORIES: biostudies-literature

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Syntheses of papyracillic acids: application of the tandem chain extension-acylation reaction.

Mazzone Jennifer R JR Zercher Charles K CK

The Journal of organic chemistry 20121005 20

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. ...[more]

PMID: 23013246

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