Abstract:The naturally occurring ten-membered lactones decarestrictine B (4) and D (5), which lower cholesterol levels, were glycosylated with deoxygenated 2-selenoglycosyl acetates 7 a, 7 b, and glycal 10 (obtained from d-glucose), and glycal 13 (obtained from l-rhamnose). Depending on the glycosylation method employed, the triol decarestrictine D was glycosylated with a high degree of regioselectivity. A set of hybrid structures were yielded by O-deblocking and in most cases reductive removal of a halogen or a phenylselenyl group from C-2 of the glycosides 14 a ± f, 20 a, 20 b, and 24. These hybrids were subjected to preliminary biological tests in which the novel glycoconjugates 15 d and 15 e displayed DNA-binding properties.
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