A synthetic approach to nomofungin/communesin B

Seth L. Crawley, Raymond Lee Funk

Research output: Contribution to journalArticle

80 Citations (Scopus)

Abstract

(Matrix presented) A highly stereoselective intramolecular cycloaddition of an indole tethered to an aza-ortho-xylylene intermediate effects the rapid construction of a substantial portion of the ring system of the cytotoxic natural product communesin B. An analogous cycloaddition involving an orthoquinone methide intermediate provides an adduct that clearly revealed that the structural assignment for nomofungin was in error.

Original languageEnglish (US)
Pages (from-to)3169-3171
Number of pages3
JournalOrganic Letters
Volume5
Issue number18
DOIs
StatePublished - Sep 4 2003

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Cycloaddition
Cycloaddition Reaction
cycloaddition
indoles
Biological Products
adducts
rings
products
matrices
nomofungin
communesin B
indole

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Crawley, Seth L. ; Funk, Raymond Lee. / A synthetic approach to nomofungin/communesin B. In: Organic Letters. 2003 ; Vol. 5, No. 18. pp. 3169-3171.
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A synthetic approach to nomofungin/communesin B. / Crawley, Seth L.; Funk, Raymond Lee.

In: Organic Letters, Vol. 5, No. 18, 04.09.2003, p. 3169-3171.

Research output: Contribution to journalArticle

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