Total synthesis of neokotalanol, a potent α-glucosidase inhibitor isolated from Salacia reticulata.
10.1016/S1875-5364(13)60079-5
- Author:
Wei-Jia XIE
1
;
Genzoh TANABE
2
;
Nozomi TSUTSUI
2
;
Xiao-Ming WU
1
;
Osamu MURAOKA
3
Author Information
1. Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China.
2. School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
3. School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. Electronic address: muraoka@phar.kindai.ac.jp.
- Publication Type:Journal Article
- Keywords:
Neokotalanol;
Salacia reticulata;
Total synthesis;
α-glucosidase inhibitor
- MeSH:
Enzyme Inhibitors;
chemical synthesis;
chemistry;
Glycoside Hydrolase Inhibitors;
Plant Extracts;
chemical synthesis;
chemistry;
Salacia;
chemistry
- From:
Chinese Journal of Natural Medicines (English Ed.)
2013;11(6):676-683
- CountryChina
- Language:English
-
Abstract:
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.
