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Stereoselective functionalization of platensimycin and platencin by sulfa-Michael/aldol reactions. 2019
Lin Qiu, and
Zhongqing Wen, and
Yuling Li, and
Kai Tian, and
Youchao Deng, and
Ben Shen, and
Yanwen Duan, and
Yong Huang
Xiangya International Academy of Translational Medicine at Central South University, Changsha, Hunan 410013, China. jonghuang@csu.edu.cn ywduan66@sina.com.
Bioinspired sulfa-Michael/aldol cascade reactions have been developed for the semisynthesis of sulfur-containing heterocyclic derivatives of platensimycin and platencin, with three newly formed contiguous stereogenic centers. Density functional theory calculations revealed the mechanism for the stereochemistry control. This method was used in a synthesis of a platensimycin thiophene analogue with potent antibacterial activities against Staphylococcus aureus.
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