Formation of five-membered carbocycles from D-glucose: A Concise Synthesis of 4-Hydroxy-2-(hydroxymethyl)cyclopentenone

Yoshitaka Koseki, Toshihiro Watanabe, Takaaki Kamishima, Eunsang Kwon, Hitoshi Kasai

研究成果: Article査読

2 被引用数 (Scopus)

抄録

A concise synthesis of 4-hydroxy-2-(hydroxymethyl)cyclo-pentenone (1) has been accomplished from D-glucose by a three-step sequence that features a catalyst-free hydrothermal reaction of D-glucal, which is readily obtained from D-glucose. Optimization of the reaction conditions for synthesizing 1 was performed by changing the temperature and reaction time. The treatment of D-glucal under the optimal conditions, i.e., at 120 °C for 24 h, provided 1 in the highest isolated yield of 61%. 1 would become a versatile intermediate for the synthesis of various fine chemicals having a cyclopentenone structure from cellulosic biomass.

本文言語English
ページ(範囲)1324-1328
ページ数5
ジャーナルBulletin of the Chemical Society of Japan
92
8
DOI
出版ステータスPublished - 2019

ASJC Scopus subject areas

  • Chemistry(all)

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