索丁多环吡喃核心的汇聚式和非对映选择性合成。

Convergent and diastereoselective synthesis of the polycyclic pyran core of saudin.

作者信息

Tambar Uttam K, Kano Taichi, Zepernick John F, Stoltz Brian M

机构信息

Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.

出版信息

J Org Chem. 2006 Oct 27;71(22):8357-64. doi: 10.1021/jo061236+.

DOI:10.1021/jo061236+

PMID:17064005

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.

摘要

天然产物索丁被发现可在小鼠中诱导低血糖，因此，它可能是开发治疗糖尿病新药物的一个有吸引力的先导结构。已开发出一种非对映选择性串联施蒂勒-氧杂电环化反应，该反应能够以快速且汇聚的方式构建索丁的核心结构。这种新反应已扩展到一系列多环吡喃体系的汇聚合成。在将这些复杂的吡喃体系转化为天然产物方面已取得进展。本文全面介绍了这些合成研究工作。