A convenient entry to C2- and C3-substituted gulono-gamma-lactone derivatives from L-ascorbic acid.
A convenient method to obtain unknown chiral C2- and C3-functionalized aldono-1,4-lactone derivatives starting from l-ascorbic acid, which would be valuable in the synthesis of derivatives of various pharmacologically active agents for structure-activity studies, is described. The practicality of this approach is demonstrated by the synthesis of a series of 5,6-O-isopropylidene-2-allyl-3-keto-l-galactono-gamma-lactone and 5,6-O-isopropylidene-3-allyl-2-keto-l-galactono-gamma-lactone derivatives using the thermal Claisen rearrangement of the corresponding 3-O- and 2-O-allyl derivatives of 5,6-O-isopropylidene-l-ascorbic acid, respectively, followed by stereospecific reduction to the corresponding alcohols. The synthetic steps are shown to be efficient, and enantiospecific, and they proceed with high yields.
Olabisi
Ayodele O
AO
Department of Chemistry, Wichita State University, Wichita, KS 67260-0051, USA.
Mahindaratne
Mathew P D
MP
Wimalasena
Kandatege
K
D001205:Ascorbic Acid / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013400:Sugar Acids / Q000737:chemistry*
D013400:Sugar Acids; C007895:gulonolactone; D001205:Ascorbic Acid