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A facile approach for the synthesis of flavans was developed by employing a BF3.Et2O-catalyzed pyran cyclization in an aprotic polar solvent as a key step, by which concise total syntheses of (+/-)-7-hydroxy-3',4'-methylenedioxyflavan (1) and (+/-)-4'-hydroxy-7-methoxyflavan (2), two naturally occurring flavans, were achieved.


Y Li, J Yang, W Z Li, L Hou, J Xue, Y Li. Studies on flavans. 1. Facile synthesis of (+/-)-7-hydroxy-3',4'-methylenedioxyflavan and (+/-)-4'-hydroxy-7-methoxyflavan by a BF3.Et2O-mediated pyran cyclization. Journal of natural products. 2001 Feb;64(2):214-6

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PMID: 11430003

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