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Total synthesis of (+)-pilosinine via a stereodivergent conjugate addition strategy.

ABSTRACT: In recent work, asymmetric conjugate addition reactions to chiral 4-phenyl-N-enoyl-1,3-oxazolidinones have been shown to give different stereochemical outcomes depending on the conditions employed. Through the application of stereodivergent reaction conditions, the total synthesis of (+)-pilosinine and the formal synthesis of (-)-pilosinine has been completed from a single enantiomer of the 1,3-oxazolidi-none auxiliary.

SUBMITTER: Schrank CL

PROVIDER: S-EPMC7288726 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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Total synthesis of (+)-pilosinine via a stereodivergent conjugate addition strategy.

Schrank Cassandra L CL Danneman Michael W MW Prebihalo Emily A EA Anderson Robert E RE Gibson Tyler J TJ Wuest William M WM Mullins Richard J RJ

Tetrahedron letters 20200418 23

In recent work, asymmetric conjugate addition reactions to chiral 4-phenyl-<i>N</i>-enoyl-1,3-oxazolidinones have been shown to give different stereochemical outcomes depending on the conditions employed. Through the application of stereodivergent reaction conditions, the total synthesis of (+)-pilosinine and the formal synthesis of (-)-pilosinine has been completed from a single enantiomer of the 1,3-oxazolidi-none auxiliary. ...[more]

PMID: 32528190

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