Teleocidins B-1-B-4 的 11 步全合成。
11-Step Total Synthesis of Teleocidins B-1-B-4.
机构信息
Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.
出版信息
J Am Chem Soc. 2019 Jan 30;141(4):1494-1497. doi: 10.1021/jacs.8b13697. Epub 2019 Jan 15.
Abstract
A unified and modular approach to the teleocidin B family of natural products is presented that proceeds in 11 steps and features an array of interesting strategies and methods. Indolactam V, the known biosynthetic precursor to this family, was accessed through electrochemical amination, Cu-mediated aziridine opening, and a remarkable base-induced macrolactamization. Guided by a desire to minimize concession steps, the tactical combination of C-H borylation and a Sigman-Heck transform enabled the convergent, stereocontrolled synthesis of the teleocidins.
摘要
本文提出了一种统一的、模块化的方法来合成 teleocidin B 天然产物家族，该方法共 11 步，具有一系列有趣的策略和方法。吲哚内酰胺 V 是该家族已知的生物合成前体，通过电化学氨化、Cu 介导的氮丙啶开环和显著的碱诱导大环内酯化反应来制备。为了尽量减少让步步骤，我们根据需要，通过 C-H 硼化和 Sigman-Heck 转化的策略组合，实现了 teleocidins 的收敛性、立体控制合成。
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