Journal of Organic Chemistry p. 3289 - 3296 (1982)
Update date:2022-08-04
Topics: Synthesis Column chromatography Enantiomerically pure Catalyst Nuclear magnetic resonance (NMR) spectroscopy Reagent High-performance liquid chromatography (HPLC) Chiral Resolution N-Acyl Derivatives C-Methyl Analogues Aminodeoxy Sugar L-Acosamine Noncarbohydrate Precursors
Fronza, Giovanni
Fuganti, Claudio
Grasselli, Piero
Majori, Luisella
Pedrocchi-Fantoni, Giuseppe
Spreafico, Franca
The 2S,3R diol 2a and the 3R α-ketol 5b, prepared in fermenting baker's yeast from cinnamaldehyde and α-methylcinnamaldehyde, are converted into the chiral N-trifluoroacetyl deoxy C-methyl-branched amino sugars 15b,c and 19b.Key intermediates in the synthesis are the C4 and C5 chiral aldehydes 9a and 17a and the α,β-unsaturated carbonyl compounds 11a and 18, which upon threo stereoselective addition of ammonia, eventually give 15b,c and 19b.The sterochemistry and the conformations of the aminodeoxy sugar derivatives and of the intermediate lactones are deduced byNMR studies.
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Doi:10.1016/S0040-4039(00)86896-3
(1982)Doi:10.1016/S0040-4039(00)87055-0
(1982)Doi:10.1016/S0040-4039(00)86843-4
(1982)Doi:10.1007/s00044-017-2110-8
(2018)Doi:10.1007/BF00909956
(1962)Doi:10.1002/psc.2869
(2016)