Cycloaddition reactions of imines with 3-thiosuccinic anhydrides: Synthesis of the tricyclic core of martinellic acid

Pui Yee Ng, Craig E. Masse, Jared T. Shaw

Research output: Contribution to journalArticle

62 Scopus citations

Abstract

Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce γ-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-π repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps.

Original languageEnglish (US)
Pages (from-to)3999-4002
Number of pages4
JournalOrganic Letters
Volume8
Issue number18
DOIs
StatePublished - Aug 31 2006
Externally publishedYes

ASJC Scopus subject areas

  • Molecular Medicine

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