Enantioselective construction of the 8-azabicyclo[3.2.1]octane scaffold: application in the synthesis of tropane alkaloids,Organic & Biomolecular Chemistry

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Enantioselective construction of the 8-azabicyclo[3.2.1]octane scaffold: application in the synthesis of tropane alkaloids
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2021-3-15 , DOI: 10.1039/d1ob00143d
Sandra Rodriguez ₁ , Uxue Uria ₁ , Efraim Reyes ₁ , Liher Prieto ₁ , Marta Rodríguez-Rodríguez ₁ , Luisa Carrillo ₁ , Jose L Vicario ₁

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The 8-azabicyclo[3.2.1]octane scaffold is the central core of the family of tropane alkaloids, which display a wide array of interesting biological activities. As a consequence, research directed towards the preparation of this basic structure in a stereoselective manner has attracted attention from many research groups worldwide across the years. Despite this, most of the approaches rely on the enantioselective construction of an acyclic starting material that contains all the required stereochemical information to allow the stereocontrolled formation of the bicyclic scaffold. As an alternative, there are a number of important methodologies reported in which the stereochemical control is achieved directly in the same transformation that generates the 8-azabicyclo[3.2.1]octane architecture or in a desymmetrization process starting from achiral tropinone derivatives. This review compiles the most relevant achievements in these areas.

中文翻译：

8-氮杂双环[3.2.1]辛烷支架的对映选择性构建：在托烷生物碱合成中的应用

8-氮杂双环[3.2.1]辛烷支架是托烷生物碱家族的核心，具有广泛的生物活性。因此，多年来，针对以立体选择性方式制备这种基本结构的研究引起了全世界许多研究小组的关注。尽管如此，大多数方法都依赖于对映选择性构建无环起始材料，该起始材料包含所有所需的立体化学信息，以允许立体控制地形成双环支架。作为替代方案，报告了许多重要的方法，其中立体化学控制直接在生成 8-氮杂双环的同一转化中实现[3.2。1]辛烷结构或从非手性托品酮衍生物开始的去对称化过程。本综述汇总了这些领域最相关的成就。

更新日期：2021-04-12

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