D-Gulonolactone as a synthon for L-noviose: first preparation of 4-O-demethyl-L-noviofuranose and related derivatives.
[reaction: see text] A new synthesis of L-noviose (11), a sugar moiety of novobiocin, is presented. D-Gulonolactone was initially converted in a few steps to the key ester derivative 7 [1-O-benzyl methyl 2,3-O-(1-methylethylidene)-alpha-L-lyxofuranosiduronate]. An appropriate selection of protecting groups enabled transformation of 7 under mild reaction conditions to 4-O-demethyl-L-noviofuranose 9a and related 9b-c. Derivatives 9 were further converted either to L-lyxopyranoses (10a and 10b) or to methyl L-lyxofuranoside 12.
Jeselnik
Marjan
M
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, SI-1000 Ljubljana, Slovenia.
Leban
Ivan
I
Polanc
Slovenko
S
Kocevar
Marijan
M
D005663:Furans / Q000737:chemistry*; D008958:Models, Molecular; D009675:Novobiocin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D010429:Pentoses / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013400:Sugar Acids / Q000737:chemistry*
D005663:Furans; D010429:Pentoses; D013400:Sugar Acids; D009675:Novobiocin; C007895:gulonolactone