One-Step Conversion to a Disubstituted Cyclopentenone from 2-Deoxy-D-Glucose and Application to Synthesis of Prostaglandin E1 Methyl Ester

被引：7

作者：

Kamishima, Takaaki ^{[1
,2
]}

Nonaka, Toshiyuki ^{[2
]}

Watanabe, Toshihiro ^{[1
]}

Koseki, Yoshitaka ^{[1
]}

Kasai, Hitoshi ^{[1
]}

机构：

[1] Tohoku Univ, Inst Multidisciplinary Res Adv Mat IMRAM, Aoba Ku, Sendai, Miyagi 9808577, Japan

[2] FromSeeds Corp, Aoba Ku, Sendai, Miyagi 9800845, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2018年 / 91卷 / 12期

关键词：

Biomass; Hydrothermal reaction; Total synthesis; HIGHLY EFFICIENT SYNTHESIS; ASYMMETRIC-SYNTHESIS; HIGH-TEMPERATURE; D-FRUCTOSE; GLUCOSE; WATER; HYDROLYSIS; PRESSURES; CELLULOSE; ACID;

D O I：

10.1246/bcsj.20180241

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 E-1 methyl ester.

引用

页码：1691 / 1696

页数：6