title: Novel synthesis of a 1,3,5-trioxazatriquinane skeleton using a nitrogen clamp.
abstract: An alpha-hydroxyaldehyde derived from naltrexone was converted to an oxazoline dimer with ammonium chloride and sodium acetate in MeOH under reflux. The resulting dimer was treated with dl-camphorsulfonic acid in CHCl(3) to give the trimer. The method for trimer synthesis was also applied to general alpha-hydroxyaldehydes to afford trimers in good yield.
authors.affiliation: School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Nagase
authors.forename: Akio
authors.initials: A
authors.lastname: Watanabe
authors.forename: Masaya
authors.initials: M
authors.lastname: Harada
authors.forename: Mayumi
authors.initials: M
authors.lastname: Nakajima
authors.forename: Ko
authors.initials: K
authors.lastname: Hasebe
authors.forename: Hidenori
authors.initials: H
authors.lastname: Mochizuki
authors.forename: Kenji
authors.initials: K
authors.lastname: Yoza
authors.forename: Hideaki
authors.initials: H
authors.lastname: Fujii
mesh_terms: D018360:Crystallography, X-Ray; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D009271:Naltrexone / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D010080:Oxazoles; D009271:Naltrexone; D009584:Nitrogen