Concise Unified Access to (-)-8-Deoxy-13-dehydroserratinine, (+)-Fawcettimine, (+)-Fawcettidine, and (-)-8-Deoxyserratinine Using a Direct Intramolecular Reductive Coupling
Concise Unified Access to (-)-8-Deoxy-13-dehydroserratinine, (+)-Fawcettimine, (+)-Fawcettidine, and (-)-8-Deoxyserratinine Using a Direct Intramolecular Reductive Coupling
复制标题
使用直接分子内还原偶联简明统一获得 (-)-8-脱氧-13-脱氢舍拉汀、( )-Fawcettimine、( )-Fawcettidine 和 (-)-8-Deoxyserratinine
DOI：
10.1021/acs.orglett.1c00977
复制
发表时间：
2021
期刊：
影响因子：
5.2
通讯作者：
Yao Zhu-Jun
中科院分区：
文献类型：
--
作者：
Zhong Lin-Rui;Huang Bing-Bing;Yang Xiao-Liang;Wang Shaozhong;Yao Zhu-Jun
公开了一种短的、可扩展的、集体全合成的四种福西替胺型石松生物碱的八步或九步合成方法。致密的多小环螺-α-氨基环戊酮成功地作为关键中间体，通过LiDBB介导的脂肪族亚胺和酯-羰基的分子内还原偶联直接获得。与采用含有九元环的经典Heathcock中间体的那些相比，新策略显示出合成步骤和氧化还原经济性的显着改进以及出色的立体化学控制。
A short, scalable, and collective total synthesis of four fawcettimine-typeLycopodiumalkaloids in eight or nine steps is disclosed. A dense multi-small-ringspiro-α-aminocyclopentanone successfully served as the key intermediate, which was directly accessed by a LiDBB-mediated intramolecular reductive coupling of the aliphatic imine and an ester-carbonyl. Compared to those that employ classical Heathcock intermediate(s) containing a nine-membered ring, the new strategy shows the significant improvement of the synthetic step and redox economies as well as excellent stereochemical control.