Concise total syntheses of variecolortides A and B through an unusual hetero-Diels-Alder reaction

Christian A. Kuttruff, Hendrik Zipse, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

A fusion of certain anthraquinones and diketopiperazines is an apt description of the variecolortides, a family of unusual fungal alkaloids. In a new, concise total synthesis of the variecolortides A and B, the natural racemates are obtained highly convergently and almost without protecting-group manipulations. The spirocyclic core is generated in a hetero-Diels-Alder reaction of a 1,4-anthraquinone with a didehydrodiketopiperazine.

Original languageEnglish (US)
Pages (from-to)1402-1405
Number of pages4
JournalAngewandte Chemie - International Edition
Volume50
Issue number6
DOIs
StatePublished - Feb 7 2011

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Diketopiperazines
Alkaloids
Anthraquinones
Fusion reactions
1,4-anthraquinone

Keywords

  • alkaloids
  • biomimetic synthesis
  • cascade reactions
  • cycloaddition
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Concise total syntheses of variecolortides A and B through an unusual hetero-Diels-Alder reaction. / Kuttruff, Christian A.; Zipse, Hendrik; Trauner, Dirk.

In: Angewandte Chemie - International Edition, Vol. 50, No. 6, 07.02.2011, p. 1402-1405.

Research output: Contribution to journalArticle

Kuttruff, Christian A. ; Zipse, Hendrik ; Trauner, Dirk. / Concise total syntheses of variecolortides A and B through an unusual hetero-Diels-Alder reaction. In: Angewandte Chemie - International Edition. 2011 ; Vol. 50, No. 6. pp. 1402-1405.
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