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基于手性可调结构单元的鸡冠花生物碱的集合合成

来源：花匠小妙招时间：2025-02-21 07:03

基于手性可调结构单元的鸡冠花生物碱的集合合成

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

摘要

我们开发出了一种基于带有手性可调结构单元的共同中间体的新策略，用于集体合成金鸡纳树碱类生物碱和杂oyohimbine 类生物碱。该合成策略的关键转变是通过顺序亲核 C-N 键形成/曼尼希式环化来构建高功能性 C/D 环，基于手性可调结构单元立体控制引入 C15 和 C20 手性中心，以及通过 Me3Al 的胺定向加成来构建 C18 甲基。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Collective Syntheses of Corynanthe Alkaloids Based on a Chirality-Tunable Structure Unit

A novel strategy based on a common intermediate bearing a chirality-tunable structure unit for the collective syntheses of corynantheine-type and heteroyohimbine-type alkaloids has been developed. Key transformations of the synthetic strategy are a sequential nucleophilic C–N bond formation/Mannich-type cyclization to construct the highly functional C/D rings, a stereocontrolled introduction of the C15 and C20 chiral centers based on the chirality-tunable structure unit, and an amine-directed addition of Me3Al to construct the C18 methyl group.

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来源期刊

Organic Letters

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.