Tetrahedron: Asymmetry

Unusual ring contraction by substitution of 4-O-activated-pentono-1, 5-lactams with cyanide. Stereospecific synthesis of 6-amino-1, 4, 5, 6-tetradeoxy-1, 4-imino- …

M Godskesen, I Lundt, I Søtofte

文献索引：Godskesen, Michael; Lundt, Inge; Sotofte, Inger Tetrahedron Asymmetry, 2000 , vol. 11, # 2 p. 567 - 579

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被引用次数: 8

摘要

Reaction of 4-O-sulfonylated 2, 3-O-isopropylidene-d-ribo-or-d-lyxo-1, 5-lactams with tetrabutylammonium cyanide gave 4-amino-5-C-cyano-4, 5-dideoxy-2, 3-O-isopropylidene-l- lyxo-5 or-l-ribo-15-1, 4-lactams, respectively. A stereospecific ring contraction with inversion at C-4 had taken place in each case. Reduction of the cyano-lactams with LiAlH4 gave 6- amino-1, 4, 5, 6-tetradeoxy-1, 4-imino-l-lyxo-6 or-l-ribo-16-hexitol, respectively. The 6- ...