title: An unexpected rearrangement of pent-4-enofuranosides to cyclopentanones upon hydrogenolysis of the anomeric benzyl group.
abstract: During our synthesis toward the unique nucleoside antibiotic A201A, we were surprised to find that a benzyl arabino-pent-4-enofuranoside underwent a Ferrier II-like rearrangement readily to provide the corresponding cyclopentanone derivative in high yield and stereoselectivity upon hydrogenolysis of the anomeric benzyl group.
authors.affiliation: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Shenyou
authors.initials: S
authors.lastname: Nie
authors.affiliation: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Xiaoping
authors.initials: X
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Yuyong
authors.initials: Y
authors.lastname: Ma
authors.affiliation: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. Electronic address: lmwave@mail.sioc.ac.cn.
authors.forename: Wei
authors.initials: W
authors.lastname: Li
authors.affiliation: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. Electronic address: byu@mail.sioc.ac.cn.
authors.forename: Biao
authors.initials: B
authors.lastname: Yu
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D001593:Benzyl Compounds / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000617:Aminoglycosides; D001593:Benzyl Compounds; D003517:Cyclopentanes; D006027:Glycosides; C007201:cyclopentanone; C046076:A 201A; D006859:Hydrogen
keywords: Cyclopentanone; Exocyclic enol ether; Ferrier II rearrangement; Furanoside; Hydrogenolysis