Total synthesis of huperserratines A and B,Organic Chemistry Frontiers

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Total synthesis of huperserratines A and B
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2022-05-24 , DOI: 10.1039/d2qo00608a
Zhen-Tao Deng _{1,

2} , Xing-De Wu ₁ , Zai-Feng Yuan ₁ , Nai-Rong Yu _{1,

2} , Yu-Fei Ou _{1,

2} , Qin-Shi Zhao ₁

Affiliation

Huperserratines A (1) and B (2), two novel macrocyclic Lycopodium alkaloids, possess an aza-12-membered ring. Here, we describe the first total synthesis of these two natural products in 12 steps. Key elements of the synthesis include the Suzuki–Miyaura coupling, the Hosomi–Sakurai reaction, ring-closing metathesis, dihydroxylation, and the Swern oxidation. A gram-scale ring-closing metathesis was pivotal in forging the challenging aza-12-membered ring. This total synthesis would enable future studies on the structure–activity relationship of 1 and 2.

中文翻译：

石杉碱甲 A 和 B 的全合成

Huperserratines A ( 1 ) 和 B ( 2 ) 是两种新型大环石松属生物碱，具有氮杂 12 元环。在这里，我们通过 12 个步骤描述了这两种天然产物的首次全合成。合成的关键要素包括 Suzuki-Miyaura 偶联、Hosomi-Sakurai 反应、闭环复分解、二羟基化和 Swern 氧化。克级闭环复分解是打造具有挑战性的 aza-12 元环的关键。这种全合成将使未来对1和2的构效关系的研究成为可能。

更新日期：2022-05-24

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