Convergent and diastereoselective synthesis of the polycyclic pyran core of saudin

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

Research output: Contribution to journalArticle

27 Citations (Scopus)

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
StatePublished - Oct 27 2006

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Pyrans
Biological Products
Medical problems
Large scale systems
saudin
Lead

ASJC Scopus subject areas

  • Organic Chemistry

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Convergent and diastereoselective synthesis of the polycyclic pyran core of saudin. / Tambar, Uttam K.; Kano, Taichi; Zepernick, John F.; Stoltz, Brian M.

In: Journal of Organic Chemistry, Vol. 71, No. 22, 27.10.2006, p. 8357-8364.

Research output: Contribution to journalArticle

Tambar, Uttam K. ; Kano, Taichi ; Zepernick, John F. ; Stoltz, Brian M. / Convergent and diastereoselective synthesis of the polycyclic pyran core of saudin. In: Journal of Organic Chemistry. 2006 ; Vol. 71, No. 22. pp. 8357-8364.
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