Convergent and Diastereoselective Synthesis of the Polycyclic Pyran Core of Saudin
The Journal of Organic Chemistry2006Vol. 71(22), pp. 8357–8364
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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 Stille-oxa-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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