A Concise Approach for Producing Optically Pure Carboxylic Acid Segments for the Synthesis of Bicyclic Depsipeptide Histone Deacetylase Inhibitors

Koichi Narita, Noel Sayar, Ken Saijo, Chikashi Ishioka, Tadashi Katoh

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Optically pure carboxylic acid segments, which are common key intermediates for the synthesis of naturally occurring bicyclic depsipeptide histone deacetylase inhibitors, have been produced efficiently. The method features the chromatographic separation of two diastereomers, which were formed by direct amide condensation of racemic (3 RS,4 E)-3-hydroxy-7-mercaptohept-4-enoic acid (rac -Hmh) with chiral amino acids. This approach offers a reliable and practical method for producing optically pure carboxylic acid segments, which can facilitate easier access to important anticancer agents derived from them.

Original languageEnglish
Pages (from-to)1408-1418
Number of pages11
JournalSynthesis (Germany)
Volume51
Issue number6
DOIs
Publication statusPublished - 2019 Jan 1

Keywords

  • bicyclic depsipeptide
  • histone deacetylase inhibitor
  • natural product
  • synthetic intermediate
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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