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Syntheses of Racemic Diaminosugar Derivatives Starting from 1,2‐Dihydropyridines and from Nitrosobenzene
Author(s) -
Augelmann Gérard,
Streith Jacques,
Fritz Hans
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680112
Subject(s) - chemistry , nitrosobenzene , hydrogenolysis , bicyclic molecule , adduct , piperidine , stereoselectivity , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Racemic diaminosugars were easily obtained by a regio‐ and stereoselective three‐step synthetis. In the first step, regiospecific hetero‐ Diels ‐ Alder cycloadditions between 1,2‐dihydropyridines 1a and 10 and nitrosobenzene led to the bicyclic compounds 2a and 11 , respectively, cis ‐Glycol formation starting from these latter adducts, followed by hydrogenolysis of the NO bond and by exhaustive acetylation of the OH‐groups, led to the diaminolyxose 5 , the diaminomannose 14 and the diaminoallose 15 . When starting from benzyl 1,2‐dihydropyridine‐1‐carboxylate ( 1b ) and using the same reaction sequence, the racemic piperidine derivative 8 was obtained.