Convergent and diastereoselective synthesis of the polycyclic pyran core of saudin.
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.
Tambar
Uttam K
UK
Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Kano
Taichi
T
Zepernick
John F
JF
Stoltz
Brian M
BM
D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D007004:Hypoglycemic Agents / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011108:Polymers / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D004224:Diterpenes; D007004:Hypoglycemic Agents; D011108:Polymers; D011714:Pyrans; C450680:saudin