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Formation of the BC ring system of upenamide via a Staudinger/aza-Wittig reaction.

ABSTRACT: The BC ring system of upenamide was assembled using a stereoselective Diels-Alder reaction followed by a Staudinger/aza-Wittig/imine hydrolysis reaction. Stereoselective aldol coupling with an aldehyde that incorporates the DE ring system led to an advanced synthetic intermediate en route to the marine alkaloid upenamide.

SUBMITTER: Luo Z

PROVIDER: S-EPMC2534099 | biostudies-literature | 2007 Nov

REPOSITORIES: biostudies-literature

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Formation of the BC ring system of upenamide via a Staudinger/aza-Wittig reaction.

Luo Zhushou Z Peplowski Katherine K Sulikowski Gary A GA

Organic letters 20071101 24

The BC ring system of upenamide was assembled using a stereoselective Diels-Alder reaction followed by a Staudinger/aza-Wittig/imine hydrolysis reaction. Stereoselective aldol coupling with an aldehyde that incorporates the DE ring system led to an advanced synthetic intermediate en route to the marine alkaloid upenamide. ...[more]

PMID: 17973484

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