Total synthesis of nepodin and torachrysone glucosides: Evidence for naturally occurring l-glucosides

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2024-07-09 DOI:10.1016/j.tetlet.2024.155191

Mizuki Makita, Ken-ichi Nihei

引用次数: 0

Abstract

The first concise synthesis of nepodin-1-O-β-d-glucopyranoside (D-1) and its l-glucopyranoside (L-1), as well as torachrysone-1-O-β-d-glucopyranoside (D-2) and its l-glucopyranoside (L-2), was achieved via Fries rearrangement and selective glycosylation. Spectral data, particularly the specific rotation signs of the synthetic l-glucosides, correlated with those of natural products previously isolated from Rumex dentatus. This confirms the presence of naturally occurring l-glucosides, L-1 and L-2, identified through synthetic approaches.

Abstract Image

查看原文本刊更多论文

肾素和山茶甙的全合成：天然存在的 l-葡萄糖苷的证据

通过弗里斯重排和选择性糖基化，首次简明地合成了山奈豆素-1-O-β-d-吡喃葡萄糖苷（D-1）及其 l-吡喃葡萄糖苷（L-1），以及山奈豆素-1-O-β-d-吡喃葡萄糖苷（D-2）及其 l-吡喃葡萄糖苷（L-2）。光谱数据，尤其是合成的 l-吡喃葡萄糖苷的特定旋转符号，与之前从鲁美克牙鲆中分离出的天然产品的光谱数据相关。这证实了通过合成方法鉴定的天然 l-葡萄糖苷 L-1 和 L-2 的存在。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.