Synthesis of (+)-Voglibose

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-15 DOI:10.1021/acs.orglett.5c0064710.1021/acs.orglett.5c00647

Camille Rocq, Vincent Hamel, Alexandra Furtos-Matei and Sylvain Canesi*,

引用次数: 0

Abstract

A concise asymmetric synthesis of voglibose, a natural product derivative and an alpha-glucosidase inhibitor with antihyperglycemic activity, was produced from an O-arylated lactic acid derivative in only seven steps. This approach was based on an oxidative phenol dearomatization process promoted by a hypervalent iodine reagent, a chiral auxiliary serving as a protecting group and allowing the asymmetric formation of the target, and a key hydrolysis leading to the formation of several contiguous stereocenters and removal of the chiral auxiliary.

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（+）-伏糖的合成

以o -芳基化乳酸衍生物为原料，通过7步合成了具有抗高血糖活性的天然产物衍生物和α -葡萄糖苷酶抑制剂voglibose。该方法基于一个氧化苯酚脱芳过程，该过程由高价碘试剂促进，一个手性助剂作为保护基团，允许目标的不对称形成，以及一个关键的水解导致几个连续的立体中心的形成和手性助剂的去除。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.