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Paper | Special issue | Vol 42, No. 2, 1996, pp.669-676
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S68
De Novo Synthesis of Racemic Altronolactam and Arabinonolactam Azasugars

Théophile Tschamber, Elsa-Maria Rodriguez-Perez, Patrick Wolf, and Jacques Streith

*Ecole Nationale Supérieure de Chimie de Mulhouse, Université de Haute Alsace, 3, Rue Alfred Werner 68093 Mulhouse Cedez, France


Starting from the known peracetylated piperidinose derivatives (7a) and (7b), the corresponding altrono- and arabinon- lactams (4) and (5) were obtained in a straightforward way. A selective two-step hydrolysis of the anomeric acetoxy groups gave the free hydroxyls (8a) and (8b) which were oxidised to the β-lactams (9a) and (9b), respectively. Deprotection of these latter compounds led to the target molecules.