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

Fingerprint

Diketopiperazines
Cycloaddition
Biological Products
Hydrogen
Oxidation
cycloaddition
Air
methylene
cascades
chemistry
oxidation
shift
air
hydrogen
synthesis
products
anthrone
variecolortide C

Keywords

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

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Evolution of a synthetic strategy for the variecolortides. / Kuttruff, Christian A.; Mayer, Peter; Trauner, Dirk.

In: European Journal of Organic Chemistry, No. 27, 09.2012, p. 5151-5161.

Research output: Contribution to journalArticle

Kuttruff, Christian A. ; Mayer, Peter ; Trauner, Dirk. / Evolution of a synthetic strategy for the variecolortides. In: European Journal of Organic Chemistry. 2012 ; No. 27. pp. 5151-5161.
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