title: Chiral pool based efficient synthesis of the aminocyclitol core and furanoside of (-)-hygromycin A: formal total synthesis of (-)-hygromycin A.
abstract: A chiral pool based synthetic strategy that leads from the readily available and inexpensive C(2)-symmetric tartaric acids to the chiral O-isopropylidenebenzooxazole--a convenient precursor to the aminocyclitol core of hygromycin A as well as the chiral γ-disilyloxybutyrolactone--a pivotal intermediate to approach to the furanoside of hygromycin A.
authors.affiliation: Department of Chemistry, National Chung-Hsing University, Taichung 400, Taiwan, Republic of China.
authors.forename: Hong-Jay
authors.initials: HJ
authors.lastname: Lo
authors.forename: Yuan-Kang
authors.initials: YK
authors.lastname: Chang
authors.forename: Tu-Hsin
authors.initials: TH
authors.lastname: Yan
mesh_terms: D002384:Catalysis; D002934:Cinnamates / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006921:Hygromycin B / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002934:Cinnamates; D006921:Hygromycin B; C026273:hygromycin A