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 | |
| State | Published - Oct 27 2006 |
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ASJC Scopus subject areas
- Organic Chemistry
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Convergent and diastereoselective synthesis of the polycyclic pyran core of saudin. / Tambar, Uttam K.; Kano, Taichi; Zepernick, John F.; Stoltz, Brian M.
In: Journal of Organic Chemistry, Vol. 71, No. 22, 27.10.2006, p. 8357-8364.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Convergent and diastereoselective synthesis of the polycyclic pyran core of saudin
AU - Tambar, Uttam K.
AU - Kano, Taichi
AU - Zepernick, John F.
AU - Stoltz, Brian M.
PY - 2006/10/27
Y1 - 2006/10/27
N2 - 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.
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.
UR - http://www.scopus.com/inward/record.url?scp=33750455502&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33750455502&partnerID=8YFLogxK
U2 - 10.1021/jo061236+
DO - 10.1021/jo061236+
M3 - Article
C2 - 17064005
AN - SCOPUS:33750455502
VL - 71
SP - 8357
EP - 8364
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 22
ER -