A Convergent Synthesis of the Tricyclic Architecture of the Guanacastepenes Featuring a Selective Ring Fragmentation

William D. Shipe, Erik J. Sorensen

Research output: Contribution to journalArticle

66 Scopus citations

Abstract

(Matrix Presented) This Letter describes a concise, diastereoselective synthesis of the tricyclic carbon framework of the guanacastepene family of natural products. An intermolecular Diels-Alder reaction established a remote stereochemical relationship and facilitated a synthesis of allylic acetate 3, which was subsequently joined with vinylstananne 9 via a Stille coupling. An intramolecular [2 + 2] photocycloaddition then afforded complex cyclobutyl ketone 19, which underwent a stereoelectronically controlled fragmentation to the guanacastepene architecture on treatment with samarium diiodide.

Original languageEnglish (US)
Pages (from-to)2063-2066
Number of pages4
JournalOrganic Letters
Volume4
Issue number12
DOIs
StatePublished - Jun 13 2002
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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