德国康斯坦茨大学Gaich, Tanja报道了了合成紫杉烷二萜的通用策略。相关研究成果于2024年6月11日发表于国际顶尖学术期刊《自然》。

任何有机分子的碳骨架都是其三维结构的基础，在决定其物理和生物性质方面发挥着关键作用。因此，紫杉烷二萜是最著名的天然产物家族之一，主要是由于其最突出的一种有效的抗癌药化合物紫杉醇的成功，且已有25年多的历史。这两组紫杉烷的碳骨架存在显著差异，因此它们通常有自己独特的合成方法。在

该文中，研究人员报道了一种基于复杂分子框架相互转化的多功能合成策略，为更广泛的紫杉烷二萜家族提供了通用途径。研究人员制备了一系列经典的和环紫杉烷骨架，其中包括由单个高级中间体首次全合成紫杉碱 K （2）、canataxapropellane （5） 和双丙烷 C 。合成方法有意避开仿生学，而是强调立体电子控制在协调多环框架的相互转换中的能力。

附：英文原文

Title: A general strategy for the synthesis of taxane diterpenes

Author: Pan, Lu, Schneider, Fabian, Ottenbruch, Moritz, Wiechert, Rainer, List, Tatjana, Schoch, Philipp, Mertes, Bastian, Gaich, Tanja

Issue&Volume: 2024-06-11

Abstract: The carbon skeleton of any organic molecule serves as the foundation for its three-dimensional structure, playing a pivotal role in determining its physical and biological properties.1As such, taxane diterpenes are one of the most well known natural product families, primarily owing to the success of their most prominent compound, paclitaxel, an effective anti-cancer therapeutic for more than 25 years.2-6 In contrast to classical taxanes, the bioactivity of cyclotaxanes (also referred to as complex taxanes) remains significantly underexplored. The carbon skeletons of these two groups of taxanes differ significantly, and so would typically their own distinct synthetic approaches. Here, we report a versatile synthetic strategy based on the interconversion of complex molecular frameworks, providing general access to the wider taxane diterpene family. A range of classical and cyclotaxane frameworks was prepared including, among others, the first total syntheses of taxinine K (2), canataxapropellane (5) and dipropellane C from a single advanced intermediate. The synthetic approach deliberately eschews biomimicry, emphasizing instead the power of stereoelectronic control in orchestrating the interconversion of polycyclic frameworks.

DOI: 10.1038/s41586-024-07675-8

Source: https://www.nature.com/articles/s41586-024-07675-8