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Total Synthesis of Ginkgolide C and Formal Syntheses of Ginkgolides A and B
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2022-09-23 , DOI: 10.1021/jacs.2c08351
Martin Hébert 1 , Gabriel Bellavance 1 , Louis Barriault 1
Affiliation  

Ginkgolides are diterpenes isolated from Ginkgo biloba that exhibit strong anti-inflammatory and neuroprotective properties. The highly complex molecular architecture of ginkgolides, combined with their remarkable biological profile, provides a unique platform for the development of new strategies and methods. Herein, we reported the first total synthesis of ginkgolide C and the formal syntheses of ginkgolides A and B. Our synthesis is based on a functional group strategy guided by the compact structure of ginkgolide, where a series of diastereoselective carbon–carbon bond formations and oxidations are carefully orchestrated.

中文翻译:

银杏内酯 C 的全合成和银杏内酯 A 和 B 的正式合成

银杏内酯是从银杏叶中分离出来的二萜,具有很强的抗炎和神经保护作用。银杏内酯高度复杂的分子结构,结合其卓越的生物学特性,为开发新的策略和方法提供了独特的平台。在此,我们报道了银杏内酯 C 的首次全合成以及银杏内酯 A 和 B 的正式合成。我们的合成基于银杏内酯紧凑结构指导的官能团策略,其中一系列非对映选择性碳-碳键形成和氧化是精心编排的。
更新日期:2022-09-23
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