斯门硫氮杂环化合物A和B的全合成

Total syntheses of smenothiazoles A and B.

作者信息

Ma Xiao, Chen Yajie, Chen Sigui, Xu Zhengshuang, Ye Tao

机构信息

Laboratory of Chemical Genomics, Engineering Laboratory for Chiral Drug Synthesis, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Xili, Nanshan District, Shenzhen, 518055, China.

出版信息

Org Biomol Chem. 2017 Aug 30;15(34):7196-7203. doi: 10.1039/c7ob01818e.

DOI:10.1039/c7ob01818e

PMID:28813067

Abstract

Concise total syntheses of smenothiazoles A (1) and B (2), two distinguished vinyl chloride containing natural products isolated from the marine sponge S. aurea, have been developed. Silastannation, Stille reaction and a carefully controlled desilylchlorination were employed as key steps to construct unique polyketide acid fragments, and the optimized reaction conditions avoided migration of 2,5-diene to a 2,4-conjugated system. This report unambiguously confirmed the structures of both natural products.

摘要

已开发出对从海洋海绵金黄色栓菌中分离出的两种独特的含氯乙烯天然产物——斯门噻唑A（1）和B（2）的简洁全合成方法。硅锡化反应、施蒂勒反应和精心控制的脱硅氯化反应被用作构建独特聚酮酸片段的关键步骤，优化后的反应条件避免了2,5-二烯迁移至2,4-共轭体系。本报告明确证实了这两种天然产物的结构。