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Polycyclic Furanobutenolide-Derived Cembranoid and Norcembranoid Natural Products: Biosynthetic Connections and Synthetic Efforts
Chemical Reviews ( IF 51.4 ) 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:


多环呋喃丁烯酸内酯衍生的西松烷和正西松烷天然产物:生物合成联系和合成努力



多环呋喃丁烯酸内酯衍生的西松烷和降西松烷天然产物是一类稠密的、立体化学复杂的、广泛氧化的多环二萜和去甲二萜。尽管自 20 世纪 90 年代分离出该家族的第一批成员以来,这些天然产物的优雅结构和生物活性特征已经引起了化学家的注意,但仅从头合成了单一多环呋喃丁烯酸内酯衍生的西松烷和去甲西松烷。 。本文首先简要讨论了拟议的生物合成以及多环呋喃丁烯内酯衍生的西松烷类和去甲西松烷类之间的生物合成联系,然后全面回顾了天然产物家族每个成员的合成工作,包括仿生、半合成和从头合成综合策略。收集这些知识是为了深入了解这些紧凑且高度氧化的多环结构的反应性和限制,并为未来的合成工作提供指导。
更新日期:2017-05-18
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