Total Synthesis of Jerangolid B via sp3-sp2 Stille Coupling.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-05 DOI:10.1021/acs.orglett.5c02569

Janick Schug,Bernd Morgenstern,Johann Jauch

引用次数: 0

Abstract

First isolated from Sorangium cellulosum So ce 307, jerangolids are a class of natural products with high antifungal activity and minimal toxicity toward mammals. Comprised of a skipped diene substructure with a chiral center in between a δ-lactone and a pyran substituent, they present an intriguing synthetic challenge. We herein report the first synthesis of jerangolid B through a modular approach that incorporates sp3-sp2 Stille coupling as the key step to generate the skipped diene structure. By comparing our synthetic jerangolid B to the data published in the literature, we could show that the configuration at C14 is R.

查看原文本刊更多论文

sp3-sp2偶联法合成Jerangolid B。

蛇兰果苷是一类天然产物，具有较高的抗真菌活性和对哺乳动物的毒性。它们由跳过的二烯亚结构组成，手性中心位于δ-内酯和吡喃取代基之间，这是一个有趣的合成挑战。本文首次采用模块化方法合成了jerangolid B，该方法将sp3-sp2 Stille偶联作为生成跳过二烯结构的关键步骤。通过将我们合成的jerangolid B与文献中发表的数据进行比较，我们可以发现C14处的构型为R。

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

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.