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Stereoselective functionalization of platensimycin and platencin by sulfa-Michael/aldol reactions

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Abstract

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.

Graphical abstract: Stereoselective functionalization of platensimycin and platencin by sulfa-Michael/aldol reactions

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Publication details

The article was received on 09 Feb 2019, accepted on 21 Feb 2019 and first published on 21 Feb 2019


Article type: Paper
DOI: 10.1039/C9OB00324J
Citation: Org. Biomol. Chem., 2019, Advance Article

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    Stereoselective functionalization of platensimycin and platencin by sulfa-Michael/aldol reactions

    L. Qiu, Z. Wen, Y. Li, K. Tian, Y. Deng, B. Shen, Y. Duan and Y. Huang, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00324J

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