Syntheses of 7a-Substituted Pyrrolizidine Derivatives via Stereocontrolled Anionic Cyclization

Synthesis Pub Date : 2024-05-06 DOI:10.1055/s-0043-1774861
Hongjun Ming, Darong He, Shengmeng Si, Chao Xu, Yunge Yuan, Xiaoran Tian, Zhigang Hu, Shikuo Li, Hui Zhang, Fangzhi Huang, Yue-Lei Chen
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Abstract

Starting from inexpensive proline and epichlorohydrin, a pivotal stereocontrolled anionic cyclization reaction paves the way for a robust and adaptable methodology to produce stereoisomers of 7a-substituted pyrrolizidine derivatives. This process yields intriguing 7a-hydroxymethyl pyrrolizidine derivatives, among them valuable trans-(2-fluorohexahydro-1H-pyrrolizin-7a-yl)methanol, which is attainable through multiple steps.

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通过立体控制阴离子环化合成 7a 取代的吡咯烷衍生物
从廉价的脯氨酸和环氧氯丙烷开始,一个关键的立体控制阴离子环化反应为生产 7a 取代的吡咯烷衍生物的立体异构体铺平了道路。这一过程产生了有趣的 7a- 羟甲基吡咯烷衍生物,其中有价值的反式-(2-氟六氢-1H-吡咯烷-7a-基)甲醇可通过多个步骤获得。
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