Conformation-Enabled Total Syntheses of Ohmyungsamycins A and B and Structural Revision of Ohmyungsamycin B

Joonseong Hur, Jaebong Jang, Jaehoon Sim, Woo Sung Son, Hee Chul Ahn, Tae Sung Kim, Yern Hyerk Shin, Changjin Lim, Seungbeom Lee, Hongchan An, Seok Ho Kim, Dong Chan Oh, Eun Kyeong Jo, Jichan Jang, Jeeyeon Lee, Young Ger Suh

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

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.

Original languageEnglish
Pages (from-to)3069-3073
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number12
DOIs
StatePublished - 12 Mar 2018

Keywords

  • cyclodepsipeptides
  • macrolactamization
  • natural products
  • structural revision
  • total synthesis

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