✍ Scribed by Richard R. Schmidt; Wendelin Frick; Brigitte Haag-Zeino; Satyam Apparao
No coin nor oath required. For personal study only.
The functionally substituted n,B-unsaturated carbonyl compounds >,b provide with styrenes and with methyl nmethoxyacrvafe in regiospecific and endo-and site-selective inverse type hetero-Die&-Alder reactions the dihydropyrans 2-4 and 2, --respectively, which are readily transformed into C-aryl-B-glucopyranosides and into methyl (methyl 3-deoxy-Rarabino-2-heptulopyranosid)onates. Thus, from achiral precursors up to five new centers of chirality are generated in a three step procedure. C-Aryl-glycosides and 3-deoxy-2-glyculosonates are wide-spread in 2-4) Nature
. The biological importance of these compounds prompted deve- lopment of several synthetic approaches. C-Aryl-glycosides were mainly obtained from glycosyl donors and activated benzene derivatives in Friedel-Crafts type reactions 4) ; however, many difficulties were encountered
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