title: 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.affiliation: Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
authors.forename: Uttam K
authors.initials: UK
authors.lastname: Tambar
authors.forename: Taichi
authors.initials: T
authors.lastname: Kano
authors.forename: John F
authors.initials: JF
authors.lastname: Zepernick
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
mesh_terms: 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
chemical_list: D004224:Diterpenes; D007004:Hypoglycemic Agents; D011108:Polymers; D011714:Pyrans; C450680:saudin