Synthesis of novel pyrrolidine 3,4-diol derivatives as inhibitors of alpha-L-fucosidases
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Reaction of aldehydes, anilines, and enecarbamates in dichloromethane in the presence of EtOH and a catalytic amt. of chiral phosphoric acid I afforded the Mannich adducts which were in situ reduced to anti-1,2-disubstituted 1,3-diamines II in excellent di ...
A new sulfur dioxide-based organic chemistry has been developed as a novel approach for the stereoselective synthesis of polyene fragments based on our one-pot, four-component synthesis of polyfunctional alpha-alkanesulfonyl-gamma,delta-unsaturated ketones ...
Efficient methods for the stereoselective synthesis of polyfunctional (E)- and (2)-alkenes and conjugated (EE)- and (E,2)-dienones are presented. They rely upon one-pot, four-component processes that condense 1-oxy-1,3-dienes, silyl enol ethers, SO2, and c ...
A concise, practical and stereoselective total synthesis of galantinic acid, constituent of the peptide antibiotic galantin, is reported. The title compound is obtained in six steps via Heathcock-Claisen condensation, Evans reduction and deprotection in 10 ...
An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural anal ...
A one-pot procedure involving radical conjugate addition of B-alkylcatecholboranes to enones followed by intramolecular aldol reaction is reported. Application to the stereoselective synthesis of monocyclic and bicyclic products with up to four contiguous ...
The ketonitrone 8 was prepared from D-fructose as an inexpensive starting material, and was used in a stereoselective synthesis of 1-deoxymannojirimycin (4), its previously unknown N-hydroxy analogue 15, as well as the polyhydroxylated ketonitrone 14. The ...
The preparation of [(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]furan derivatives in a stereoselective route starting from D-glucose and ethyl acetoacetate is presented. Ethyl ester (6), N,N-diethylamide (7) and N-isopropylamide (8) have been tested towards 25 ...
N-Benzyloxycarbonyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-L-ribose 12a has been converted into (1R,2S,6R, 7S,7aS)-5 and (1R, 2S, 6S, 7R, 7aR)-1,2,6,7-tetrahydroxypyrrolidin-5-ones 6 and (1R,2S,6S,7S,7aS)-7 and (1R,2S,6R,7R,7aS)-1,2,6,7-tetrahydroxypyr ...
Two successive brominations of 8-oxabicyclo[3.2.1]oct-6-en-2-one 6 provided 3-exo,6-exo,7-endo-tribromo-7oxabicyclo[3.2.1]octan-2-endo-one 10 with high stereoselectivity. NaBH4 reduced 10 into 3-exo, 6-exo,7-endo-tribromo-8-oxabicyclo[3.2.1]octan-2-endo-ol ...