One-Step conversion to a disubstituted cyclopentenone from 2-Deoxy-D-Glucose and application to synthesis of prostaglandin e1 methyl ester

Takaaki Kamishima, Toshiyuki Nonaka, Toshihiro Watanabe, Yoshitaka Koseki, Hitoshi Kasai

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

We have developed a facile one-step conversion of 2-deoxy-D-glucose to form a disubstituted cyclopentenone through catalyst-free hydrothermal reaction under mild conditions. The use of 2-deoxy-D-glucose in one-pot conversion is to provide the formation of a carbon five-membered ring instead of the common biomass-derived furans such as furfural, 5-HMF, etc. The cyclopentenone has a potential to be a building block for the preparation of chemical products. As one example, we successfully demonstrated the synthesis of prostaglandin E1 methyl ester.

Original languageEnglish
Pages (from-to)1691-1696
Number of pages6
JournalBulletin of the Chemical Society of Japan
Volume91
Issue number12
DOIs
Publication statusPublished - 2018

Keywords

  • Biomass
  • Hydrothermal reaction
  • Total synthesis

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