凋亡诱导素酮的对映选择性合成：利用噻唑烷硫酮手性助剂的多功能性

Enantioselective synthesis of apoptolidinone: exploiting the versatility of thiazolidinethione chiral auxiliaries.

作者信息

Crimmins Michael T, Christie Hamish S, Chaudhary Kleem, Long Alan

机构信息

Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.

出版信息

J Am Chem Soc. 2005 Oct 12;127(40):13810-2. doi: 10.1021/ja0549289.

DOI:10.1021/ja0549289

PMID:16201800

Abstract

An efficient, enantioselective synthesis of apoptolidinone has been completed, demonstrating the versatility of thiazolidinethione auxiliaries. Three propionate aldol additions and two asymmetric glycolate alkylations function to establish 8 of the 12 stereogenic carbon centers. A cross-metathesis reaction is utilized to assemble the C1-C10 trieneoate fragment and the C11-C28 polypropionate region of the molecule.

摘要

已完成对凋亡诱导素酮的高效对映选择性合成，证明了噻唑烷硫酮助剂的多功能性。三次丙酸酯羟醛加成反应和两次不对称乙醇酸烷基化反应用于构建12个手性碳中心中的8个。利用交叉复分解反应组装分子的C1-C10三烯酸酯片段和C11-C28多丙酸酯区域。