title: Palladium(II)-catalyzed cyclization of urethanes and total synthesis of 1-deoxymannojirimycin.
abstract: The palladium(II)-catalyzed cyclization of the urethane 8, which was derived from D-mannitol, gave the cyclic compound 9 with excellent diastereoselectivity. During these transformations, the Pd(II) species are not reduced and thus the catalyst can recycle without its reoxidation. The cycloadduct 9 was converted to 1-deoxymannojirimycin.
authors.affiliation: Department of Chemistry, Faculty of Science, Toyama University, 3190 Gofuku, Toyama 930-8555, Japan. hirai@sci.toyama-u.ac.jp
authors.forename: H
authors.initials: H
authors.lastname: Yokoyama
authors.forename: K
authors.initials: K
authors.lastname: Otaya
authors.forename: H
authors.initials: H
authors.lastname: Kobayashi
authors.forename: M
authors.initials: M
authors.lastname: Miyazawa
authors.forename: S
authors.initials: S
authors.lastname: Yamaguchi
authors.forename: Y
authors.initials: Y
authors.lastname: Hirai
mesh_terms: D017485:1-Deoxynojirimycin / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D010165:Palladium; D014520:Urethane / Q000737:chemistry*
chemical_list: D007202:Indicators and Reagents; D017485:1-Deoxynojirimycin; D014520:Urethane; D010165:Palladium