Radical-initiated cyclization as a key step for the synthesis of oxoprotoberberine alkaloids |
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Authors: | Chih-Shone Lee Tsung-Ching Yu Yen-Yao Cheng |
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Affiliation: | 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 |
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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. |
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Keywords: | Alkaloids Oxoprotoberberine Radical-initiated cyclization |
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