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A tandem Prins/Schmidt reaction approach to marine alkaloids: formal and total syntheses of lepadiformines A and C.

ABSTRACT: The tricyclic core of the cylindricine or lepadiformine families of alkaloid natural products was assembled via a Prins addition/intramolecular Schmidt rearrangement under Lewis acid conditions. Both single-pot and two-stage variations of this process were examined, with particular attention to the stereochemical outcome of the processes. This technology has been applied to a formal total synthesis of lepadiformine A and a total synthesis of lepadiformine C.

SUBMITTER: Meyer AM

PROVIDER: S-EPMC2846845 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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A tandem Prins/Schmidt reaction approach to marine alkaloids: formal and total syntheses of lepadiformines A and C.

Meyer Angelica M AM Katz Christopher E CE Li Sze-Wan SW Vander Velde David D Aubé Jeffrey J

Organic letters 20100301 6

The tricyclic core of the cylindricine or lepadiformine families of alkaloid natural products was assembled via a Prins addition/intramolecular Schmidt rearrangement under Lewis acid conditions. Both single-pot and two-stage variations of this process were examined, with particular attention to the stereochemical outcome of the processes. This technology has been applied to a formal total synthesis of lepadiformine A and a total synthesis of lepadiformine C. ...[more]

PMID: 20178342

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