A. Corsaro, V. Pistarà, G. Catelani
Sep 11, 2006
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0
Influential Citations
18
Citations
Journal
Tetrahedron Letters
Abstract
Abstract The stereoselective transformation of the cyclopropyl derivative 2, stereoselectively obtained with the Simmons–Smith reaction of methyl 2,6-di-O-benzyl-α- l -threo-hex-4-enopyranoside (1), into gabosines and deoxy-carbahexoses is described. The treatment of 2 with mercuric trifluoroacetate in dry methanol gives the organomercuric chloride 3, which by demercuration with lithium aluminum hydride affords the 4-C-deoxy-4-methyl-1,5-bis-glycoside 4. The acid hydrolysis of 4 produces a mixture of the two diastereoisomeric 2-methyl-cyclohex-2-enones 6 and 7, catalytically reduced to carba-sugars 10 and 11. Structures and stereochemistry of all isolated compounds were determined by 1D and 2D NMR experiments.