Evolution of a synthetic strategy for the variecolortides

Christian A. Kuttruff, Peter Mayer, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

The variecolortides are a family of unusual natural products that combine motifs from a variety of biosynthetic streams. Herein, we present the gradual evolution of a convergent synthetic strategy that ultimately culminated in a reaction cascade featuring a hydrogen shift and a cycloaddition followed by a spontaneous air oxidation. Attempts to link an anthrone building block with an exo-methylene diketopiperazine using radical chemistry were ultimately unsuccessful, but led to interesting observations that shaped our successful strategy. The total synthesis of variecolortide C is presented for the first time.

Original languageEnglish (US)
Pages (from-to)5151-5161
Number of pages11
JournalEuropean Journal of Organic Chemistry
Issue number27
DOIs
StatePublished - Sep 2012

Keywords

  • Biomimetic synthesis
  • Cascade reactions
  • Cycloaddition
  • Domino reactions
  • Natural products
  • Total synthesis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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