Abstract
The base-catalyzed cyclizations of tri- O-acetyl-1,7-dibromo-1,7-dideoxy- xylo-2,6-heptodiulose ( 2), tri- O-acetyl-1,7-dichloro-1,7-dideoxy- xylo-2,6-heptodiulose ( 3), and tri- O-acetyl-1,7-di- C-azido-1,7-dideoxy- xylo-2,6-heptodiulose ( 4), to dL-4,5,6-tri- O-acetyl-2- C-bromo-3-C-(bromomethyl)- 2, 3, 4, 6/ 5-tetrahydroxycyclohexanone ( 5), dL-4,5,6-tri- O-acetyl-2-chloro-3- C-(chloromethyl)- 2, 3, 4, 6/ 5-tetrahydroxycyclohexanone ( 6), and dL-4,5,6-tri- O-acetyl-2- C-azido-3- C-(azidomethyl)- 2, 3, 4, 6/ 5-tetrahydroxycyclohexanone ( 7), respectively, are described. Reduction of the acetylated cycloses 5–7 by sodium borohydride proceeded with considerable stereoselectivity in producing branched epi-inositols, isolated as the tetraacetates 12, 13, and 18. These latter compounds were used to prepare the corresponding unprotected cyclitols 24, 25, and 31, and the branched amino- epi-inositols 27, 29, 30, and 32. The stereochemistry of the branched-chain cyclitols described appears to be the same as that of dL-1,4,5,6-tetra- O-acetyl-3-chloro-2- C-(chloromethyl)- epi-inositol ( 13), whose structure was confirmed by an X-ray crystallographic study.
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