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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 9: 3297 - 3303

DOI: https://doi.org/10.6023/cjoc202304032

  • Junjie Zhang ,
  • Xuetao Xu
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  • School of Biotechnology and Health Science, Wuyi University, Jiangmen, Guangdong 529020
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Received date: 2023-04-25

  Revised date: 2023-05-19

  Online published: 2023-05-25

Supported by

Department of Education of Guangdong Province(2021KCXTD044)

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Abstract

Tetrahydroprotoberberine alkaloids have good bioactivity against malaria and epilepsy, among them, xylopinine has good anti malaria activity, while laudanosine has epilepsy treatment activity. A concise asymmetric synthesis of ( S)-(–)- xylopinine and ( S)-(+)-laudanosine has been reported. The key strategies include diastereoselective nucleophilic addition to N-tert-butanesulfinimine, which is combined with Pictet-Spengler reaction as a key step for constructing the pivotal tetrahydroprotoberberine skeleton. This strategy provides a concise and rapid approach to ( S)-(–)-xylopinine (7 steps and 11.1% overall yield) and ( S)-(+)-laudanosine (7 steps and 16.4% overall yield) from known starting materials. The S configuration of synthetic xylopinine and laudanosine at C(14) is confirmed by comparing their specific rotation data.

Key words： xylopinine; laudanosine; N-tert-butanesulfinimine; asymmetric addition

Cite this article

Junjie Zhang , Xuetao Xu . [J]. Chinese Journal of Organic Chemistry, 2023 , 43(9) : 3297 -3303 . DOI: 10.6023/cjoc202304032

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