A synthesis of (+)-FR182877, featuring tandem transannular Diels-Alder reactions inspired by a postulated biogenesis

David A. Vosburg, Christopher D. Vanderwal, Erik J. Sorensen

Research output: Contribution to journalArticle

104 Scopus citations

Abstract

An efficient biomimetic synthesis of the reported structure of the hexacyclic, cytotoxic secondary metabolite FR182877 is described. The successful route features the synthesis of a 19-membered ring carbocycle using two π-allyl palladium(II)-mediated C-C bond-forming reactions. This polyunsaturated macrocycle undergoes tandem transannular Diels-Alder reactions that create five rings and seven stereogenic centers in one operation under mild conditions, representing the first double transannular Diels-Alder reaction. The absolute stereochemistry of the natural product is demonstrated to be opposite of that reported previously. Significant quantities of both enantiomers of this microtubule-stabilizing natural product and related structures are now available via this approach.

Original languageEnglish (US)
Pages (from-to)4552-4553
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number17
DOIs
StatePublished - May 1 2002
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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