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.
Additional Information
© 2006 American Chemical Society. Received 15 June 2006. Published online 4 October 2006. Published in print 1 October 2006. The authors are grateful to the California Institute of Technology, NSF-PECASE, NDSEG (graduate fellowship to U.K.T.), the Japan Society for the Promotion of Science (postdoctoral fellowship to T.K.), Bristol-Myers Squibb, Merck, Abbott, Amgen, Lilly, Pfizer, and GlaxoSmithKline for generous financial support. Dr. John H. Phillips and Mr. Galen Loram are acknowledged for experimental assistance. We thank Mr. Larry M. Henling and Dr. Michael W. Day for X-ray crystallographic expertise.Attached Files
Supplemental Material - jo061236_2Bsi20060620_014252.cif
Supplemental Material - jo061236_2Bsi20060620_014315.cif
Supplemental Material - jo061236_2Bsi20060620_014338.cif
Supplemental Material - jo061236_2Bsi20060901_075757.pdf
Supplemental Material - jo061236_2Bsi20060901_080142.pdf
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Additional details
- Eprint ID
- 74508
- Resolver ID
- CaltechAUTHORS:20170223-142410037
- Caltech
- NSF
- National Defense Science and Engineering Graduate (NDSEG) Fellowship
- Japan Society for the Promotion of Science (JSPS)
- Bristol-Myers Squibb
- Merck
- Abbott
- Amgen
- Lilly
- Pfizer
- GlaxoSmithKline
- Created
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2017-02-23Created from EPrint's datestamp field
- Updated
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2021-11-11Created from EPrint's last_modified field