Diastereoselective synthesis of 2,3,6-trisubstituted tetrahydropyran-4-ones via prins cyclizations of enecarbamates: A formal synthesis of (+)-ratjadone A

Kimberly N. Cossey, Raymond L. Funk

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Abstract

Enecarbamates are shown to be excellent terminating groups for Prins cyclizations. A noteworthy feature of this methodology is the easy, stereoselective construction of the cyclization precursors by alkylation of metalated (E)-enecarbamates with epoxides. The stereochemistry of the resultant trisubstituted (E)-enecarbamates is then transferred with high fidelity to afford the frequently observed and biologically significant all-cis-2,3,6-trisubstituted tetrahydropyran substructures of naturally occurring compounds. Other substituted tetrahydropyrans, including 2,3,5,6-tetrasubstituted, cis-2,3-disubstituted, and cis-2,6-disubstituted, are also accessible. This methodology facilitated an exceptionally concise formal total synthesis of the nuclear export inhibitor (+)-ratjadone A.

Original languageEnglish (US)
Pages (from-to)12216-12217
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number39
DOIs
Publication statusPublished - Oct 6 2004

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All Science Journal Classification (ASJC) codes

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

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