doi:10.6023/cjoc202304032

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (9): 3297-3303.DOI: 10.6023/cjoc202304032 Previous Articles Next Articles

(S)-(–)-Xylopinine和(S)-(+)-Laudanosine的不对称合成

张俊杰, 徐学涛^*()

五邑大学生物科技与大健康学院广东江门 529020

收稿日期:2023-04-25 修回日期:2023-05-19 发布日期:2023-05-23
通讯作者: 徐学涛
基金资助:
广东省教育厅基金(2021KCXTD044)

Junjie Zhang, Xuetao Xu()

School of Biotechnology and Health Science, Wuyi University, Jiangmen, Guangdong 529020

Received:2023-04-25 Revised:2023-05-19 Published:2023-05-23
Contact: Xuetao Xu
Supported by:
Department of Education of Guangdong Province(2021KCXTD044)

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

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

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Fig. & Tab. 5

Figure 1. Structures of xylopinine and laudanosine

Scheme 1. Representative strategies for construction of tetrahydroprotoberberine skeleton

Scheme 2. Retrosynthetic analysis of xylopinine and laudanosine

Scheme 3. Synthesis of compounds 4 and 5

Scheme 4. Enantioselective synthesis of xylopinine (1) and laudanosine (2)

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(S)-(–)-Xylopinine和(S)-(+)-Laudanosine的不对称合成

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