Novel synthesis of a 1,3,5-trioxazatriquinane skeleton using a nitrogen clamp.
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.
Nagase
Hiroshi
H
School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
Watanabe
Akio
A
Harada
Masaya
M
Nakajima
Mayumi
M
Hasebe
Ko
K
Mochizuki
Hidenori
H
Yoza
Kenji
K
Fujii
Hideaki
H
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*
D006576:Heterocyclic Compounds, 4 or More Rings; D010080:Oxazoles; D009271:Naltrexone; D009584:Nitrogen