An approach to the total synthesis of the marine ascidian metabolite perophoramidine via a halogen-selective tandem heck/carbonylation strategy

Gerald D. Artman, Steven M. Weinreb

Research output: Contribution to journalArticle

75 Scopus citations

Abstract

(Matrix presented) A halogen-selective tandem intramolecular Heck/carbonylation reaction has been developed for the construction of the C,E,F-ring system and the C20 quaternary center found in perophoramidine (1). This process can be effected in good yields in the presence of both the chlorine and bromine atoms found in the natural product. In addition, it is possible to introduce the quaternary center at C4 in a stereoselective manner by a lactone enolate alkylation, using NaH and allyl bromide.

Original languageEnglish (US)
Pages (from-to)1523-1526
Number of pages4
JournalOrganic Letters
Volume5
Issue number9
DOIs
StatePublished - May 1 2003

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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