Synthesis from D-glucose

Subsequent hydrolysis with TFA gave the key intermediate 16. Oxidation of 16 with bromine in aqueous dioxane containing barium carbonate followed by removal of the protecting groups afforded 2 in 18% yield from 12. 

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Kojic acid, 5-hydroxy-2-(hydroxymethyl)-4//-pyran-4-one1 (II), is produced from carbohydrate sources in an aerobic process by a variety of microorganisms. The acid was discovered in 1907, its structure was established in 1924, and its chemical synthesis from D-glucose was achieved in 1930. Since then, a considerable amount of study has been devoted to the biosynthesis of kojic acid, and numerous publications have dealt with its chemical and biological properties. After nearly half a century, kojic acid remains a scientists curiosity, without industrial importance. It con-... 

The paradigmatic hexosaminidase inhibitor with basic nitrogen in the ring, 2-acetamido-1,2-dideoxynojirimycin (2-acetamido-l,2,5-trideoxy- 1,5-imino-D-glucitol, 33) has not been found naturally to date. This inhibitor was first prepared by Fleet and co-workers [76,77] in a 17-step synthesis from D-glucose via methyl 3-0-benzyl-2,6-dideoxy-2,6-imino-a-D-mannopyranoside together... 

Loewus, F.A., Kelly, S., and Hiatt, H.H., 1960. Ascorbic acid synthesis from D-glucose-2-14C in the liver of the intact rat. J. Biol. Chem. 235 937-939. 

Fleet, G W J, Shaw, A N, Evans, S V, Fellows, L E, Synthesis from D-glucose of 1,5-dideoxy-1,5-imino-L-fucitol, a potent a-L-fucosidase inhibitor, J. Chem. Soc. Chem., Commun., 841-842, 1985. 

Pougny, J R, Sinay, P, (35,45) -methylheptan-3-ol, a pheromone component of the smaller european aim bark beetle synthesis from D-glucose, J. Chem. Res., 1, 1982. 

Synthesis from d-glucose A stereospecific synthesis of nectrisine (1) has been achieved from diacetone D-glucose by conversion to 3 (Scheme 1). Catalytic reduction of 3 followed by acylation with trifluoroacetic anhydride afforded the trifluoroacetyl amides 4 (82%) and 5 (13%). Removal of the isopropylidene group from 4 afforded 6, which was subjected to oxidation with NaI04 followed by removal of the benzyl group and subsequent deacylation of the formyl and trifluoroacetyl groups to produce 1. 

Synthesis from d-glucose A synthesis of the fragment 3 of azinomycin has been... 

Synthesis from D-glucose Syntheses of ajmalicine (1) and 19- p/-ajmalicine... 

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