Concise, stereocontrolled synthesis of the citrinadin B core architecture

Carlos A. Guerrero, Erik J. Sorensen

Research output: Contribution to journalArticle

22 Scopus citations

Abstract

A concise, stereocontrolled synthesis of the citrinadin B core architecture from scalemic, readily available starting materials is disclosed. Highlights include ready access to both cyclic tryptophan tautomer and trans-2,6- disubstituted piperidine fragments, an efficient, stereoretentive mixed Claisen acylation for the coupling of these halves, and further diastereoselective carbonyl addition and oxidative rearrangement for assembly of the core.

Original languageEnglish (US)
Pages (from-to)5164-5167
Number of pages4
JournalOrganic letters
Volume13
Issue number19
DOIs
StatePublished - Oct 7 2011

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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