Collective Syntheses of 8-Oxoprotoberberines via Sequential In(OTf)3-Catalyzed Cyclization and Pd(OAc)2-Catalyzed Heck Coupling.
Collective Syntheses of 8-Oxoprotoberberines via Sequential In(OTf)3-Catalyzed Cyclization and Pd(OAc)2-Catalyzed Heck Coupling.
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DOI：
10.1021/acs.joc.3c00419
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发表时间：
2023-05
期刊：
影响因子：
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通讯作者：
Zenghui Sun;Xinhang Zhang;Jiayue Fu;Lianjie Zhang;Maosheng Cheng;Lu Yang;Yongxian Liu
中科院分区：
文献类型：
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作者：
Zenghui Sun;Xinhang Zhang;Jiayue Fu;Lianjie Zhang;Maosheng Cheng;Lu Yang;Yongxian Liu
分四步合成了六种8-氧代原小檗碱，收率令人满意（14-19%），其中产物8-氧代小檗碱、8-氧代假小檗碱、8-氧代小檗碱和8-氧代假小檗碱来自于天然。该合成路线以In(OTf)3催化环化和Heck偶联为特色。此外，还通过8-氧化小檗碱的多种还原反应合成了天然产物小檗碱、卡那丁和安伯汀，为此类生物碱的合成提供了一种简洁的方法。
Six 8-oxoprotoberberines were synthesized collectively in four steps with acceptable yields (14-19%), of which the products 8-oxopalmatine, 8-oxopseudopalmatine, 8-oxoberberine, and 8-oxopseudoberberine come from nature. The synthetic route was featured with the In(OTf)3-catalyzed cyclization and Heck coupling. Moreover, the syntheses of the natural products berberine, canadine, and iambertine were achieved via various reductions from 8-oxoberberine, which provided a concise approach to the syntheses of this kind of alkaloids.