Convergent and diastereoselective synthesis of the polycyclic pyran core of saudin.

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.

• Authors: Uttam K Tambar, Taichi Kano, John F Zepernick, Brian M Stoltz
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 71 Issue 22 Pg. 8357-64 (Oct 27 2006) ISSN: 0022-3263 [Print] United States
• PMID: 17064005 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.)

Chemical References

• Diterpenes
• Hypoglycemic Agents
• Polymers
• Pyrans
• saudin

Topics

• Cyclization
• Diterpenes (chemical synthesis, chemistry)
• Hypoglycemic Agents (chemical synthesis, chemistry)
• Molecular Structure
• Polymers (chemistry)
• Pyrans (chemical synthesis, chemistry)
• Stereoisomerism