Convergent and diastereoselective synthesis of the polycyclic pyran core of saudin

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

doi:10.1021/jo061236+

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 journal › Article › peer-review

29 Scopus citations

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 language	English (US)
Pages (from-to)	8357-8364
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	71
Issue number	22
DOIs	https://doi.org/10.1021/jo061236+
State	Published - Oct 27 2006

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Organic Chemistry

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AU - Zepernick, John F.

AU - Stoltz, Brian M.

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AB - 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.

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Convergent and diastereoselective synthesis of the polycyclic pyran core of saudin

Abstract

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