Tetracyclic Diterpenoid Synthesis Facilitated by ODI-Cascade Approaches to Bicyclo[3.2.1]octane Skeletons,Accounts of Chemical Research

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Tetracyclic Diterpenoid Synthesis Facilitated by ODI-Cascade Approaches to Bicyclo[3.2.1]octane Skeletons
Accounts of Chemical Research ( IF 16.4 ) Pub Date : 2021-01-28 , DOI: 10.1021/acs.accounts.0c00798
Kai Gao ₁ , Jialei Hu ₂ , Hanfeng Ding _{1,

2}

Affiliation

Tetracyclic diterpenoids (C₂₀) mainly refer to the plant terpenoids bearing biogenetically related carbon skeletons derived from copalyl diphosphates (ent-CPP and syn-CPP). This large family contains over 1600 known members that can be categorized into 11 major structural types. Among them, more than three-quarters share a bridged bicyclo[3.2.1]octane subunit, which is also an important branching point in biosynthesis en route to the other types of bicyclic scaffolds, such as bicyclo[2.2.2]-, bicyclo[3.3.0]-, and tricyclo[3.2.1.0]octanes. Combined with the significance of its stereochemical importance in biological activity, the assembly of the bicyclo[3.2.1]octane skeletons is critical to the success of the whole synthesis blueprint toward tetracyclic diterpenoids. Although a number of inspiring methodologies have been disclosed, general approaches by the incorporation of innovative cascade reactions permitting access to diverse structural types of tetracyclic diterpenoids remain limited and in urgent demand.

中文翻译：

ODI级联方法促进双环[3.2.1]辛烷骨架的四环二萜合成

四环二萜类化合物（C ₂₀）主要是指带有生物遗传相关的碳骨架的植物类萜，该碳骨架来源于二棕榈酸钴（ent -CPP和syn-CPP）。这个大家族包含1600多个已知成员，可以分为11种主要结构类型。其中，四分之三以上的分子共享桥联的双环[3.2.1]辛烷亚基，这也是生物合成中通往其他类型的双环支架（例如双环[2.2.2]-，双环）的重要分支点。 [3.3.0]-和三环[3.2.1.0]辛烷。结合其立体化学重要性对生物活性的重要性，双环[3.2.1]辛烷骨架的组装对于整个合成蓝图对四环二萜的成功与否至关重要。尽管已经公开了许多启发性的方法，但是通过引入创新的级联反应使进入四环二萜类化合物的各种结构类型的通用方法仍然受到限制并且迫切需要。

更新日期：2021-02-16

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