title: Total synthesis of neokotalanol, a potent α-glucosidase inhibitor isolated from Salacia reticulata.
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.
authors.affiliation: Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China.
authors.forename: Wei-Jia
authors.initials: WJ
authors.lastname: Xie
authors.affiliation: School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
authors.forename: Genzoh
authors.initials: G
authors.lastname: Tanabe
authors.affiliation: School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
authors.forename: Nozomi
authors.initials: N
authors.lastname: Tsutsui
authors.affiliation: Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China.
authors.forename: Xiao-Ming
authors.initials: XM
authors.lastname: Wu
authors.affiliation: School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. Electronic address: muraoka@phar.kindai.ac.jp.
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D065089:Glycoside Hydrolase Inhibitors; D010936:Plant Extracts / Q000138:chemical synthesis* / Q000737:chemistry; D049918:Salacia / Q000737:chemistry*
chemical_list: D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D010936:Plant Extracts
keywords: Neokotalanol; Salacia reticulata; Total synthesis; α-glucosidase inhibitor