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Convergent and Diastereoselective Synthesis of the Polycyclic Pyran Core of Saudin

Tambar, Uttam K. and Kano, Taichi and Zepernick, John F. and Stoltz, Brian M. (2006) Convergent and Diastereoselective Synthesis of the Polycyclic Pyran Core of Saudin. Journal of Organic Chemistry, 71 (22). pp. 8357-8364. ISSN 0022-3263. https://resolver.caltech.edu/CaltechAUTHORS:20170223-142410037

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jo061236+DOIArticle
http://pubs.acs.org/doi/suppl/10.1021/jo061236%2BRelated ItemSupporting Information
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
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.
Funders:
Funding AgencyGrant Number
CaltechUNSPECIFIED
NSFUNSPECIFIED
National Defense Science and Engineering Graduate (NDSEG) FellowshipUNSPECIFIED
Japan Society for the Promotion of Science (JSPS)UNSPECIFIED
Bristol-Myers SquibbUNSPECIFIED
MerckUNSPECIFIED
AbbottUNSPECIFIED
AmgenUNSPECIFIED
LillyUNSPECIFIED
PfizerUNSPECIFIED
GlaxoSmithKlineUNSPECIFIED
Issue or Number:22
Record Number:CaltechAUTHORS:20170223-142410037
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170223-142410037
Official Citation:Convergent and Diastereoselective Synthesis of the Polycyclic Pyran Core of Saudin Uttam K. Tambar, Taichi Kano, John F. Zepernick, and Brian M. Stoltz The Journal of Organic Chemistry 2006 71 (22), 8357-8364 DOI: 10.1021/jo061236+
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:74508
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:23 Feb 2017 22:58
Last Modified:15 Jun 2020 20:04

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