engleski

Regioselective 2-Imino-1, 3-thiazolidine vs. 2-Imino-1, 3-oxazolidine Formation from the Vicinalsec-Amino Alcohol of Desosamine

In order to optimize Mukaiyama reagent-induced cyclization of vicinal sec-amino alcohols of desosamine origin towards exclusive formation of N′-substituted-2-imino-1, 3-thiazolidines via a thiocarbamoyl intermediate, the influence of reaction conditions was studied. A novel, mild, one-pot, two-step method was developed, and the formation of N′-substituted-2-imino-1, 3-oxazolidines as side products was minimized. The inversion of configuration at C-2′ was unambiguously established using NMR-based conformational analysis. A reaction mechanism was proposed. A test series of novel desosamine-modified 14- and 15-membered macrolides, bearing N′-alkyl-2-imino-1, 3-thiazolidines fused to the desosamine sugar were prepared.

Medicinal chemistry / Macrocycles / Heterocycles / Amino alcohols / Cyclization

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