title: An efficient semi-synthesis of 1-hydroxyl oleanolic acid analogs.
abstract: An efficient route for the semi-synthesis of either 1α- or 1β-OH epimers of 1-hydroxy-3-deoxyolean-12-en-28-oic acid (1), 6-8 steps from oleanolic acid is reported. The synthesis involves stereoselective formation of α,β-unsaturated epoxy ketone and subsequent Wharton reaction as key steps, offering a new access to the 1-O-substituted oleanolic acid-type pentacyclic triterpenoids.
authors.affiliation: a State Key Laboratory of Bioactive Substances and Functions of Natural Medicines , Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College , Beijing 100050 , China.
authors.forename: Da-Hui
authors.initials: DH
authors.lastname: Zhang
authors.affiliation: a State Key Laboratory of Bioactive Substances and Functions of Natural Medicines , Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College , Beijing 100050 , China.
authors.forename: Wei-Shuo
authors.initials: WS
authors.lastname: Fang
authors.affiliation: a State Key Laboratory of Bioactive Substances and Functions of Natural Medicines , Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College , Beijing 100050 , China.|b Center for Drug Evaluation , Beijing 100038 , China.
authors.forename: Shao-Rong
authors.initials: SR
authors.lastname: Wang
mesh_terms: D017665:Hydroxyl Radical / Q000737:chemistry*; D015394:Molecular Structure; D009828:Oleanolic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D017665:Hydroxyl Radical; D009828:Oleanolic Acid
keywords: 1-hydroxy-3-deoxyolean-12-en-28-oic acid; Oleanolic acid; Wharton reaction; semi-synthesis