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

• Published in: Chinese journal of natural medicines Vol. 11; no. 6; pp. 676 - 683
• Main Authors: XIE, Wei-Jia, TANABE, Genzoh, TSUTSUI, Nozomi, WU, Xiao-Ming, MURAOKA, Osamu
• Format: Journal Article
• Language: English
• Published: China Elsevier B.V 01.11.2013
• Subjects: 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; Salacia reticulata; α-glucosidase inhibitor; Neokotalanol; Total synthesis
• ISSN: 1875-5364; 1875-5364
• DOI: 10.1016/S1875-5364(13)60079-5

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.