Total syntheses of leuconoxine, leuconodine B, and melodinine e by oxidative cyclic aminal formation and diastereoselective ring-closing metathesis

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Abstract

Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]diazafenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxylindolenine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and diastereoseletive ring-closing metathesis of a triene derivative.

Original languageEnglish
Pages (from-to)2526-2529
Number of pages4
JournalOrganic letters
Volume16
Issue number9
DOIs
Publication statusPublished - 2014 May 2

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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