Enantiomerically Pure 7-Oxabicyclo[2.2.1]Hept-5-En-2-Yl Derivatives as Synthetic Intermediates .16. Total Asymmetric-Synthesis of 6-Deoxy-5-C-Methyl-D-Ribo-Hexose Structure in Aqueous-Solution
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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 ...
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 ...
The stereoselective synthesis of new 3,4-dihydroxypyrrolidine derivatives starting from D-mannose, D-ribose and L-fucose is presented. Two synthetic strategies employing organometallic addition to hemiacetalic sugars followed by selective nucleophilic disp ...
Transfer of chirality during the build-up of molecules has been applied innumerable times in organic chemistry since the end of the 19th century, when it was introduced in the so-called asymmetric synthesis by E. Fischer. Although analogous reactions were ...
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 ...
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 ...
Triacetate of 7-oxabicyclo[2.2.1]hept-5-ene-1,2-exo,3-exo-trimethanol was converted selectively into (1RS,2SR,5RS,6RS)-4,5,6-tris(acetoxymethyl)-2-bromocyclohex-3-en-1-ol (4) or into (1RS,2SR,5RS,6RS)-5,6-bis(acetoxymethyl)-2-bromo-4-bromomethylcyclohex-3 ...
Herein is reported an investigation towards the stereoselective synthesis of inherently chiral pseudorotaxanes. Chiral ammonium threads were readily prepared in five steps from racemic or enantiopure (M or P) salts of di-n-propyl-1,13-dimethoxyquinacridini ...
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 ...
A unique and practical synthetic sequence for rapid access to polyketides and to further the spiroacetals derived from them, which utilizes a bidirectional Hosomi-Sakurai allylation approach around key allylsilanes in the synthesis of the AB and CD ring sy ...
