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Radical-initiated cyclization as a key step for the synthesis of oxoprotoberberine alkaloids
Authors:Chih-Shone Lee  Tsung-Ching Yu  Yen-Yao Cheng
Institution:a Department of Chemistry, National Sun Yat-Sen University, Kaohsiung 80424, Taiwan, ROC
b Department of Chemistry, National Cheng Kung University, Tainan 70101, Taiwan, ROC
Abstract:The oxoprotoberberine alkaloids 1a-d have been synthesized efficiently from the enamide derivatives 2a-d by a radical-initiated cyclization reaction utilizing n-Bu3SnH/AIBN and CuCl. The enamide derivatives 2a-d were prepared from phenylethylamine analogues 5a-b, followed by acylation with acetic anhydride, Bischler-Napieralski cyclization with POCl3 and benzoylation with the corresponding bromobenzoyl chloride, respectively.
Keywords:Alkaloids  Oxoprotoberberine  Radical-initiated cyclization
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