The National Research Center for Carbohydrate Synthesis

Ziyang Chengguanzhen, China

The National Research Center for Carbohydrate Synthesis

Ziyang Chengguanzhen, China
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Liu L.,The National Research Center for Carbohydrate Synthesis | Hu Y.,The National Research Center for Carbohydrate Synthesis | Liu H.,The National Research Center for Carbohydrate Synthesis | Liu D.-Y.,The National Research Center for Carbohydrate Synthesis | And 3 more authors.
European Journal of Organic Chemistry | Year: 2017

Based on the application of phase-transfer-catalysis and Yu glycosylations, the first total syntheses of the arylnaphthyl glycosides phyllanthusmin D and 4′′-O-acetylmananthoside B, which have been claimed to be ideal antitumoral lead compounds in terms of cytotoxicity, cytotoxic selectivity, and a new mechanism of action, were achieved. Starting from easily accessible compounds, the two target molecules were obtained with longest linear sequences of 9 and 15 steps, in overall yields of 29 and 9 %, respectively. As part of this synthetic investigation, an efficient and scalable synthetic route to diphyllin was established, and the atropisomeric phenomenon in the arylnaphthyl glycosides was also confirmed. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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