Tetrahedron p. 2199 - 2210 (1984)
Update date:2022-07-30
Topics:
Jaeger, Volker
Schohe, Rudolf
1,3-Dipolar cycloaddition of nitrile oxides, generated from nitroethanol and nitroacetaldehyde derivatives 3, 21 and 22, respectively, and of benzonitrile oxide to 4-vinyldioxolanes 1,2 gave ca 4:1 erythro/threo mixtures of corresponding isoxazolines.LAH reduction of erytho isoxazolines proceeded with similar (ca4:1) selectivity to furnish protected ribo-amino-polyols 11, 15, 19, DL- and D-lividosamines 31 and 33, respectively, as main products.The DL-lividosamine derivative 33 was obtained pure by crystallization.In the D-series, the corresponding ribo/arabino mixture D-31/D-32 was transformed to the known α-methyl D-lividosaminide D-37.
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