±茉莉素内酯的对映选择性全合成

Enantioselective total synthesis of +-jasplakinolide.

作者信息

Ghosh Arun K, Moon Deuk Kyu

机构信息

Departments of Chemistry and Medicinal Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.

出版信息

Org Lett. 2007 Jun 7;9(12):2425-7. doi: 10.1021/ol070855h. Epub 2007 May 8.

DOI:10.1021/ol070855h

PMID:17488037

Abstract

An enantioselective total synthesis of (+)-jasplakinolide is described. The synthesis of the polyketide template utilized a diastereoselective syn-aldol, ortho-ester Claisen rearrangement followed by efficient conversion to a cyanide. The beta-amino acid unit was constructed in a highly diastereoselective manner utilizing nucleophilic addition to a chiral sulfinimine. Yamaguchi macrocyclization and removal of the protecting group provided a convenient access to (+)-jasplakinolide.

摘要

描述了（+）-茉莉酮酸内酯的对映选择性全合成。聚酮模板的合成利用了非对映选择性顺式羟醛反应、原酸酯克莱森重排，随后高效转化为氰化物。β-氨基酸单元通过对手性亚磺酰亚胺的亲核加成以高度非对映选择性的方式构建。山口大环化和保护基的去除为获得（+）-茉莉酮酸内酯提供了便利途径。