Total synthesis of neokotalanol, a potent α-glucosidase inhibitor isolated from Salacia reticulata

Neokotalanol, a potent α-glucosidase inhibitor isolated from Salacia reticulata, was synthesized through a key coupling reaction between a perbenzylated thiosugar and an appropriately protected perseitol triflate derived from D-mannose. This key step was found to be quite temperature dependent, and...

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Veröffentlicht in:	Chinese journal of natural medicines 2013-11, Vol.11 (6), p.676-683
Hauptverfasser:	XIE, Wei-Jia, TANABE, Genzoh, TSUTSUI, Nozomi, WU, Xiao-Ming, MURAOKA, Osamu
Format:	Artikel
Sprache:	eng
Schlagworte:	alpha-glucosidase Celastraceae enzyme inhibitors Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Glycoside Hydrolase Inhibitors medicinal plants Neokotalanol Plant Extracts - chemical synthesis Plant Extracts - chemistry Salacia - chemistry Salacia reticulata temperature Total synthesis α-glucosidase inhibitor
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Beschreibung
Zusammenfassung:	Neokotalanol, a potent α-glucosidase inhibitor isolated from Salacia reticulata, was synthesized through a key coupling reaction between a perbenzylated thiosugar and an appropriately protected perseitol triflate derived from D-mannose. This key step was found to be quite temperature dependent, and a simultaneous cyclization of the triflate leading to a characteristic 2,4,7-trioxabicyclo[4.2.1]nonane system was detected.
ISSN:	1875-5364 1875-5364
DOI:	10.1016/S1875-5364(13)60079-5