Intramolecular vinyl quinone Diels-Alder reactions

Asymmetric entry to the cordiachrome core and synthesis of (-)-isoglaziovianol

Florian Löbermann, Lara Weisheit, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

A short and asymmetric entry to the core structure of the cordiachromes has been developed, allowing access to (-)-isoglaziovianol in seven steps. Our synthesis includes a Trost asymmetric allylic alkylation and a reaction cascade triggered by a vinyl quinone Diels-Alder reaction and followed by intramolecular nucleophilic interception.

Original languageEnglish (US)
Pages (from-to)4324-4326
Number of pages3
JournalOrganic Letters
Volume15
Issue number17
DOIs
StatePublished - Sep 6 2013

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interception
Diels-Alder reactions
alkylation
Alkylation
Cycloaddition Reaction
quinones
entry
cascades
synthesis
isoglaziovianol
benzoquinone

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Intramolecular vinyl quinone Diels-Alder reactions : Asymmetric entry to the cordiachrome core and synthesis of (-)-isoglaziovianol. / Löbermann, Florian; Weisheit, Lara; Trauner, Dirk.

In: Organic Letters, Vol. 15, No. 17, 06.09.2013, p. 4324-4326.

Research output: Contribution to journalArticle

Löbermann, Florian ; Weisheit, Lara ; Trauner, Dirk. / Intramolecular vinyl quinone Diels-Alder reactions : Asymmetric entry to the cordiachrome core and synthesis of (-)-isoglaziovianol. In: Organic Letters. 2013 ; Vol. 15, No. 17. pp. 4324-4326.
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