Conformation‐Enabled Total Syntheses of Ohmyungsamycins A and B and Structural Revision of Ohmyungsamycin B. (21st February 2018)

• Record Type: Journal Article
• Authors: Hur, Joonseong; Jang, Jaebong; Sim, Jaehoon; Son, Woo Sung; Ahn, Hee‐Chul; Kim, Tae Sung; Shin, Yern‐Hyerk; Lim, Changjin; Lee, Seungbeom; An, Hongchan; Kim, Seok‐Ho; Oh, Dong‐Chan; Jo, Eun‐Kyeong; Jang, Jichan; Lee, Jeeyeon; Suh, Young‐Ger
• Is Part Of: Angewandte Chemie. Volume 130:Number 12(2018)
• Page Start: 3123
• Page End: 3127
• Publication Date: 2018-02-21
• Subjects: Cyclodepsipeptide -- Makrolactamisierung -- Naturstoffe -- Strukturrevision -- Totalsynthese; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201711286
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The first total syntheses of the bioactive cyclodepsipeptides ohmyungsamycin A and B are described. Key features of our synthesis include the concise preparation of a linear cyclization precursor that consists of N ‐methyl amides and non‐proteinogenic amino acids, and its macrolactamization from a bent conformation. The proposed structure of ohmyungsamycin B was revised based on its synthesis. The cyclic core of the ohmyungsamycins was shown to be responsible for the excellent antituberculosis activity, and ohmyungsamycin variants with truncated chains were evaluated for their biological activity.