A flexible approach to stereoisomeric indolizidine and quinolizidine alkaloids was developed. The strategy involves regio- and stereoselective cycloadditions of alkylidenemorpholinones 1  with cyclic nitrones to provide spiro-isoxazolidines 2  . These are converted into stereochemically similar or dissimilar indolizidine or quinolizidine motifs depending on the nitrone and the substituent on the dipolarophile. Application of the methodology in the synthesis of (+)-epitashiromine (3  ), (+)-tashiromine (4  ) and (+)-epilupinine (5  ?) will be described.

Stereochemically flexible approach to quinolizidine and indolizidine alkaloid motifs: Synthesis of (+)-epitashiromine, (+)-tashiromine, and (+)-epilupinine

248th National Meeting (2014)

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