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Polycyclic Furanobutenolide-Derived Cembranoid and Norcembranoid Natural Products: Biosynthetic Connections and Synthetic Efforts
Chemical Reviews ( IF 62.1 ) Pub Date : 2017-05-18 00:00:00 , DOI: 10.1021/acs.chemrev.7b00083
Robert A. Craig 1 , Brian M. Stoltz 1
Affiliation  

The polycyclic furanobutenolide-derived cembranoid and norcembranoid natural products are a family of congested, stereochemically complex, and extensively oxygenated polycyclic diterpenes and norditerpenes. Although the elegant architectures and biological activity profiles of these natural products have captured the attention of chemists since the isolation of the first members of the family in the 1990s, the de novo synthesis of only a single polycyclic furanobutenolide-derived cembranoid and norcembranoid has been accomplished. This article begins with a brief discussion of the proposed biosyntheses and biosynthetic connections among the polycyclic furanobutenolide-derived cembranoids and norcembranoids and then provides a comprehensive review of the synthetic efforts toward each member of the natural product family, including biomimetic, semisynthetic, and de novo synthetic strategies. This body of knowledge has been gathered to provide insight into the reactivity and constraints of these compact and highly oxygenated polycyclic structures, as well as to offer guidance for future synthetic endeavors.

中文翻译:

多环呋喃丁烯内酯衍生的类ran和类ce类天然产物:生物合成的联系和合成的努力。

多环呋喃丁烯内酯衍生的类和降冰片类天然产物是一类拥挤的,立体化学复杂的且被广泛氧化的多环二萜和降二萜。自从1990年代第一批成员分离以来,尽管这些天然产物的优雅结构和生物学活性特征已引起化学家的注意,但仅从多环呋喃丁烯内酯衍生的类和降冰片中的从头合成就已经完成。 。本文首先简要讨论拟议的生物合成以及多环呋喃丁烯内酯衍生的mb类和降冰片类中的生物合成联系,然后全面综述了对天然产物家族的每个成员的合成努力,包括仿生,半合成和从头合成策略。已经收集了这些知识,以洞悉这些紧凑和高度氧化的多环结构的反应性和约束条件,并为将来的合成工作提供指导。
更新日期:2017-05-18
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