title: Nitro-polyols via Pyridine Promoted C═C Cleavage of 2-Nitroglycals. Application to the Synthesis of (-)-Hyacinthacine A1.
abstract: A mild and convenient transformation for the synthesis of nitro-polyols is described. The nitro-polyol derivatives were prepared either from 2-nitroglycals via a pyridine-promoted scission of the carbon-carbon double bond or from glycals via a sequential nitration-scission procedure. The generated nitro-polyols could undergo a stereoselective Michael addition reaction. The utility of the addition products was exemplified by the concise synthesis of (-)-hyacinthacine A1 and 7a-epi-(-)-hyacinthacine A1.
authors.affiliation: School of Pharmaceutical Science and Technology, Tianjin University , Tianjin, 300072, China.|State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Xue Yuan Road No. 38, Beijing, 100191, China.
authors.forename: Shengbiao
authors.initials: S
authors.lastname: Tang
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Xue Yuan Road No. 38, Beijing, 100191, China.
authors.forename: De-Cai
authors.initials: DC
authors.lastname: Xiong
authors.affiliation: School of Pharmaceutical Science and Technology, Tianjin University , Tianjin, 300072, China.
authors.forename: Shende
authors.initials: S
authors.lastname: Jiang
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Xue Yuan Road No. 38, Beijing, 100191, China.
authors.forename: Xin-Shan
authors.initials: XS
authors.lastname: Ye
mesh_terms: D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*; D011134:Polysaccharides / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D009574:Nitro Compounds; D011108:Polymers; D011134:Polysaccharides; D011725:Pyridines; D011763:Pyrrolizidine Alkaloids; C508850:hyacinthacine A1; C024617:polyol; C023666:pyridine