Convergent and diastereoselective synthesis of the polycyclic pyran core of saudin

Uttam K. Tambar, Taichi Kano, John F. Zepernick, Brian M. Stoltz

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Abstract

The natural product saudin was found to induce hypoglycemia in mice and, therefore, could be an appealing lead structure for the development of new agents to treat diabetes. A diastereoselective tandem Stilleoxa- electrocyclization reaction has been developed which provides access to the core structure of saudin in a rapid and convergent manner. This new reaction has been extended to the convergent preparation of a series of polycyclic pyran systems. Progress has been made on the advancement of these complex pyran systems toward the natural product. A complete account of these synthetic efforts is presented.

Original languageEnglish (US)
Pages (from-to)8357-8364
Number of pages8
JournalJournal of Organic Chemistry
Volume71
Issue number22
DOIs
Publication statusPublished - Oct 27 2006

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ASJC Scopus subject areas

  • Organic Chemistry

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