Stereospecific Total Synthesis of Two 5-Amino-5, 6-dideoxy-DL-hexonic Acids, a Novel Class of Aminosugar Related Compounds

B Belleau, YK Au-Young

文献索引：Belleau,B.; Au-Young,Y.-K. Journal of the American Chemical Society, 1963 , vol. 85, p. 64 - 71

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被引用次数: 38

摘要

The stereospecific total synthesis of 5-amino-5, 6-dideoxy-~~-allonic acid XVII and 5-arnino- 5, 6-dideoxy-~~-gulonic acid XXVI is described. The reaction sequence involves a Diels- Alder condensation between methyl sorbate and 1-chloro-1-nitrosocyclohexane V to give the adduct VI. The structure and configuration of the latter was established by its conversion to the new aminoacid XI and to 6-methyl-3-piperidinol XIII, which was shown to possess ...