Alain Martin

Synthèse et réactivité vis-à-vis de réactifs nucléophiles des méthyl-3,4-anhydro-2,6-didésoxy-α- et -β-l-lyxo- et -ribo-hexopyranosides

Abstract The ring-opening reactions of methyl 3,4-anhydro-2,6-dideoxy-α- and -β- l - lyxo - and - ribo -hexopyranosides with sodium azide, ammonia, methyl- and dimethylamine, and sodium methoxide were studied. Regioselectivity is explained in terms of steric and conformational factors.

Synthèse de disaccharides naturels, fragments d'anthracyclines oligosaccharidiques

Abstract Methyl 2,6-dideoxy-4-O-(2,3,6-trideoxy-α- l -glycero-hexopyranosyl-4-ulose)-β- l -lyxo-hexopyranoside and methyl 2,6-dideoxy-4-O-(2,3,6-trideoxy-α- l -erythro-hexopyranosyl)-β- l -lyxo-hexopyranoside, fragments of C→B type of trisaccharides naturally occurring in antitumor anthracycline antibiotics, were prepared starting from 4-O-acetyl- l -amicetal and methyl 3-O-benzyl-2-deoxy-β- l -fucopyranoside in five and four steps, respectively.

Synthèse des méthyl-2,4,6-tridésoxy-4-trifluoroacétamido-l-hexopyranosides. Accès à de nouvelles anthracyclines

Abstract The four diastereoisomeric methyl 2,4,6-trideoxy-4-trifluoroacetamido- l -hexopyranosides have been synthesized. Coupling of the corresponding 1- O -acetyl-3- O -benzoyl- l - lyxo and 1- O -acetyl-3- O - p -nitrobenzoyl- l - arabino derivatives with daunomycinone in the presence of p -toluensulfonic acid as catalyst afforded two new anthracyclines.

Synthesis of a trisaccharide related to the antitumour antibiotic, aclacinomycin A

Trisaccharide (14), closely related to the trisaccharide moiety of aclacinomycin A has been synthesized stereoselectively by coupling (3) and (5) under Koenigs–Knorr conditions and then (7) and (9) in the presence of N-iodosuccinimide.