title: Asymmetric stereodivergent strategy towards aminocyclitols.
abstract: A concise asymmetric synthesis of aminocyclitols, such as diastereomeric 2-deoxystreptamine analogues and conduramine A, is described. The Pd-catalyzed asymmetric desymmetrization of meso 1,4-dibenzolate enables the synthesis of highly oxidized cyclohexane architectures. These scaffolds can potentially be used to access new aminoglycoside antibiotics and enantiomerically pure α-glucosidase inhibitors.
authors.affiliation: Department Of Chemistry, Stanford University, Stanford, CA (USA). bmtrost@stanford.edu.
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Sushant
authors.initials: S
authors.lastname: Malhotra
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003510:Cyclohexanes / Q000737:chemistry; D003511:Cyclohexanols / Q000138:chemical synthesis / Q000737:chemistry*; D003514:Cyclohexylamines / Q000138:chemical synthesis / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D005959:Glucosidases / Q000037:antagonists & inhibitors / Q000378:metabolism; D006595:Hexosamines / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D003510:Cyclohexanes; D003511:Cyclohexanols; D003514:Cyclohexylamines; D004791:Enzyme Inhibitors; D006595:Hexosamines; C545152:conduramine A-1; C506365:Cyclohexane; D010165:Palladium; D005959:Glucosidases; C007265:2-deoxystreptamine
keywords: aminoglycoside; azidization; conduramines; palladium; synthetic methods