title: Asymmetric syntheses of 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine.
abstract: Asymmetric syntheses of both 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine, polyhydroxylated indolizidine alkaloids that act as selective glycosidase inhibitors, have been accomplished in seven steps. The key feature of our unique syntheses includes the stereoselective introduction of the C-3 and C-4 hydroxyl groups utilizing the aza-Claisen rearrangement-induced ring expansion of 1-acyl-2-alkoxyvinyl pyrrolidine and a substrate-controlled stereoselective transannulation of the resulting azoninone intermediate.
authors.affiliation: College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Korea.
authors.forename: Hwayoung
authors.initials: H
authors.lastname: Yun
authors.forename: Jongmin
authors.initials: J
authors.lastname: Kim
authors.forename: Jaehoon
authors.initials: J
authors.lastname: Sim
authors.forename: Sujin
authors.initials: S
authors.lastname: Lee
authors.forename: Young Taek
authors.initials: YT
authors.lastname: Han
authors.forename: Dong-Jo
authors.initials: DJ
authors.lastname: Chang
authors.forename: Dae-Duk
authors.initials: DD
authors.lastname: Kim
authors.forename: Young-Ger
authors.initials: YG
authors.lastname: Suh
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D054836:Indolizidines / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D054836:Indolizidines; D007212:Indolizines; C065905:1-deoxycastanospermine