title: A versatile strategy for divergent and diastereoselective synthesis of natural product-like polyhydroxylated indolizidines.
abstract: A general and versatile method for the divergent and diastereoselective synthesis of polyhydroxylated indolizidines has been established. The annulation reactions of a readily available enantiopure dihydroxylated cyclic secondary enamine with alpha,beta-unsaturated carboxylates including methyl acrylate, methyl crotonate, methyl 2-hexenoate, allenoate, and dimethyl acetylenedicarboxylate and with malonyl chloride produced hexahydro- or tetrahydro-5-indolizinone-8-carboxylates in high yields. The resulting 5-indolizinone derivatives were converted into diverse polyhydroxylated indolizidines in good yields through practical hydrogenation and reduction reactions.
authors.affiliation: Chemistry Department, Beijing Normal University, Beijing 100875, China.
authors.forename: Xiao-Ping
authors.initials: XP
authors.lastname: Jiang
authors.forename: Ying
authors.initials: Y
authors.lastname: Cheng
authors.forename: Gao-Feng
authors.initials: GF
authors.lastname: Shi
authors.forename: Zhi-Mei
authors.initials: ZM
authors.lastname: Kang
mesh_terms: D000588:Amines / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis; D002264:Carboxylic Acids / Q000737:chemistry; D006865:Hydrogenation; D006900:Hydroxylation; D007212:Indolizines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D001688:Biological Products; D002264:Carboxylic Acids; D007212:Indolizines