Total syntheses of (+)- and (-)-1-deoxynojirimycin (1,5-dideoxy-1,5-imino-D- and L-glucitol) and of (+)- and (-)-1-deoxyidonojirimycin (1,5-dideoxy-1,5-imino-D- and L-iditol) via furoisoxazoline-3-aldehydes
C. Schaller et al., Total syntheses of (+)- and (-)-1-deoxynojirimycin (1,5-dideoxy-1,5-imino-D- and L-glucitol) and of (+)- and (-)-1-deoxyidonojirimycin (1,5-dideoxy-1,5-imino-D- and L-iditol) via furoisoxazoline-3-aldehydes, CARBOHY RES, 314(1-2), 1998, pp. 25-35
The isoxazoline obtained by 1,3-dipolar cycloaddition of 2,2-diethoxyaceton
itrile N-oxide to furan was converted into enantiomerically pure (-)-(3aS,5
S,6S,6aR)- and (+)-(3aR,5R,6R,6aS)-3a,5,6,6a-tetrahydro-5,6-isopropylidened
ioxyfuro [2,3-d]isoxazole-3-carbaldehyde, (-)-5 and (+)-5, respectively, th
rough resolution with (1S,2S)-1,2-diphenylethylenediamine. The aldehydes 5
are required as latent 1,5-iminohexitol moieties in cross-aldolizations tow
ards imino-C-disaccharides. In order to establish absolute configurations o
f 5, and to probe the projected uses, (+)-5 was converted into(+)-1-deoxyno
jirimycin [(+)-1, 3 steps, 58%] and into(-)-1,5-dideoxy-1,5-imino-L-iditol
[(-)-2, 4 steps, 40%] adopting stereoselective routes. Similarly, (-)-1,5-d
ideoxy-1,5-imino-L-glucitol ((-)-1) and (+)-1,5-dideoxy-1,5-imino-D-iditol
((+)-2) were obtained with the same ease. (C) 1998 Elsevier Science Ltd. Al
l rights reserved.