Khalil Bennis, P. Calinaud, J. Gelas
Nov 1, 1994
Citations
0
Influential Citations
13
Citations
Journal
Carbohydrate Research
Abstract
Abstract d -Ribono-1,4-lactone, after acetalation, tritylation, and reduction, leads to a cyclization compound which gave with tosyl chloride 1,4-anhydro-2,3- O -isopropylidene-5- O -trityl- d -ribitol. The latter was transformed (acid hydrolysis, periodate oxidation, reduction, tritylation, and tosylation) into a ditosylated derivative 16 , which was cyclized into morpholines by the action of primary amines. Acid hydrolysis, followed by acetylation, gives the (2 S )-acetoxymethyl-4-isopropyltetrahydro-1,4-oxazine ( 21 ). A similar sequence has been applied to d -gulonolactone to give access to oxazines 33 , 34 , and 35 .