Total synthesis of the sesquiterpene (±)-illudin C via an intramolecular nitrile oxide cycloaddition

Ronald A. Aungst, Collin Chan, Raymond Lee Funk

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

(Equation presented) A convergent total synthesis of illudin C is described. The tricyclic ring system of the natural product was quickly assembled from cyclopropane and cyclopentene precursors via a novel oxime dianion coupling reaction and a subsequent intramolecular nitrile oxide-olefin cycloaddition.

Original languageEnglish (US)
Pages (from-to)2611-2613
Number of pages3
JournalOrganic Letters
Volume3
Issue number16
DOIs
StatePublished - Aug 9 2001

Fingerprint

Cyclopentanes
Nitriles
cyclopropane
Oximes
Cycloaddition
Sesquiterpenes
nitriles
Cycloaddition Reaction
cycloaddition
Alkenes
Biological Products
Oxides
alkenes
oxides
rings
synthesis
products
illudin C

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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abstract = "(Equation presented) A convergent total synthesis of illudin C is described. The tricyclic ring system of the natural product was quickly assembled from cyclopropane and cyclopentene precursors via a novel oxime dianion coupling reaction and a subsequent intramolecular nitrile oxide-olefin cycloaddition.",
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Total synthesis of the sesquiterpene (±)-illudin C via an intramolecular nitrile oxide cycloaddition. / Aungst, Ronald A.; Chan, Collin; Funk, Raymond Lee.

In: Organic Letters, Vol. 3, No. 16, 09.08.2001, p. 2611-2613.

Research output: Contribution to journalArticle

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AU - Aungst, Ronald A.

AU - Chan, Collin

AU - Funk, Raymond Lee

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AB - (Equation presented) A convergent total synthesis of illudin C is described. The tricyclic ring system of the natural product was quickly assembled from cyclopropane and cyclopentene precursors via a novel oxime dianion coupling reaction and a subsequent intramolecular nitrile oxide-olefin cycloaddition.

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