A stereodivergent access to naturally occurring aminocarbasugars from (Phenylsulfonyl)-7-oxa-bicyclo [2.2.1] heptane derivatives. Total synthesis of (±)-Validamine and its C1 and C2 stereoisomers
Arjona, O. and Plumet, J.
Departamento de Química Orgánica. Facultad de Química, Universidad Complutense, 28040 Madrid (Spain).
Ars Pharm.36;(3);445-454, (1995)
Key words: Carbasugars, Estereocontrolled epoxidation, ValidamineAbstract
The total syntheses of the antibiotic validamine an its three diastereomers have been acomplished and their racemic penta-N-O-acetates via stereocontrolled nucleophilic epoxidation of polihydroxylated cyclohexenyl sulfones, obtained from (phenylsulphonyl)-7- oxabicyclo [2.2.1] heptanes. The diastereoselectivity of the epoxidation can be readily controlled by carufel choice of the hydroxyl protecting group. Ring opening of the resulting epoxisulfones followed by stereocontrolled introduction of an amine precursor led to the four C-1 and C-2 diastereomers of the 1-aminocarbasugars.
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