Convergent, enantioselective syntheses of guanacastepenes A and E featuring a selective cyclobutane fragmentation

William D. Shipet, Erik J. Sorensen

Research output: Contribution to journalArticle

75 Scopus citations

Abstract

The evolution of a convergent strategy that led to efficient, enantioselective syntheses of both natural (+)- and unnatural (-)-guanacastepene E and formal total syntheses of (+)- and (-)-guanacastepene A is described. A union of five- and six-membered ring intermediates by an efficient π-allyl Stille cross-coupling reaction was followed by an intramolecular enone-olefin [2 + 2] photocycloaddition and a stereoelectronically controlled, reductive fragmentation of the resulting cyclobutyl ketone. The latter two transformations enabled controlled formation of the C-11 quaternary stereocenter and the central seven-membered ring of the guanacastepenes. An enantiospecific synthesis of the functionalized five-membered ring vinyl stannane from the monoterpene R-(-)-carvone featuring a carbon-carbon bond forming ring contraction was also developed.

Original languageEnglish (US)
Pages (from-to)7025-7035
Number of pages11
JournalJournal of the American Chemical Society
Volume128
Issue number21
DOIs
StatePublished - May 31 2006

All Science Journal Classification (ASJC) codes

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

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