A facile synthesis of (+)/(−)-pentenomycin I and analogs, and their antimicrobial evaluation

Takaaki Kamishima, Masato Suzuki, Shigenobu Aoyagi, Toshihiro Watanabe, Yoshitaka Koseki, Hitoshi Kasai

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

This study reported a stereoselective synthesis of (+)/(+)-pentenomycin I in 4–5 steps through regioselective silylation, optical resolution and dihydroxylation, followed by an olefin formation, from a known racemic cyclopentenone prepared from 2-deoxy-D-glucose. We also accomplished the transformation of a common intermediate into a variety of analogs. In addition, the antimicrobial activities of the pentenomycin analogs were evaluated, which revealed important structural factors of pentenomycins for the antimicrobial activities.

Original languageEnglish
Pages (from-to)1375-1378
Number of pages4
JournalTetrahedron Letters
Volume60
Issue number20
DOIs
Publication statusPublished - 2019 May 16

Keywords

  • Antimicrobial susceptibility testing
  • Pentenomycin
  • Structure-activity relationships
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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