Strategies and Lessons Learned from Total Synthesis of Taxol,Chemical Reviews

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Strategies and Lessons Learned from Total Synthesis of Taxol
Chemical Reviews ( IF 51.4 ) Pub Date : 2023-03-14 , DOI: 10.1021/acs.chemrev.2c00763
Long Min ₁ , Jing-Chun Han ₁ , Wen Zhang ₁ , Chen-Chen Gu ₁ , Yun-Peng Zou ₁ , Chuang-Chuang Li _{1,

2}

Affiliation

Taxol (paclitaxel), the most well-known taxane diterpenoid, is the best-selling natural-source anticancer drug ever produced and one of the most common prescriptions in the treatment of breast, lung, and ovarian cancers, saving countless lives around the world. Structurally, Taxol possesses a highly oxygenated [6–8–6–4] core bearing 11 stereocenters, seven of which are contiguous chiral centers. Moreover, the extremely strained bicyclo[5.3.1] undecane ring system with a bridgehead double bond is a unique structural feature. All these features make Taxol a highly challenging synthetic target. Tremendous synthetic efforts from more than 60 research groups around the world have already culminated in ten total syntheses and three formal syntheses, as well as more than 60 synthetic model studies of Taxol. This review is intended to provide a long-overdue appraisal of the great achievements in the total syntheses of Taxol reported in the last few decades. In doing so, we summarize the development of synthesis toward Taxol from 1994 to 2022, including the evolution of synthetic strategy for accessing this complex molecular scaffold and key lessons learned from such endeavors. Finally, we briefly discuss the future of the research in this area.

中文翻译：

紫杉醇全合成的策略和经验教训

紫杉醇（紫杉醇）是最著名的紫杉烷二萜类化合物，是有史以来最畅销的天然来源抗癌药，也是治疗乳腺癌、肺癌和卵巢癌最常用的处方药之一，挽救了全世界无数人的生命. 在结构上，紫杉醇具有高度氧化的 [6-8-6-4] 核，带有 11 个立体中心，其中七个是连续的手性中心。此外，具有桥头双键的极度紧张的双环[5.3.1]十一烷环系统是一个独特的结构特征。所有这些特性使紫杉醇成为极具挑战性的合成目标。来自世界各地 60 多个研究小组的巨大合成努力已经完成了 10 个全合成和 3 个正式合成，以及 60 多个紫杉醇合成模型研究。本综述旨在对过去几十年报道的紫杉醇全合成方面的巨大成就进行期待已久的评估。在此过程中，我们总结了 1994 年至 2022 年紫杉醇合成的发展，包括获得这种复杂分子骨架的合成策略的演变以及从这些努力中吸取的重要经验教训。最后，我们简要讨论了该领域研究的未来。

更新日期：2023-03-14

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