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An asymmetric synthesis of substituted piperidines has been described.b-Cyclodextrin- or oxazaborolidine-catalyzed asymmetric reduction ofa-azido aryl ketones to the corresponding alcohols has been employed as the key step along with ring closing metathesis and selective dihydroxylation. Substituted piperidines (polyhydroxy piperidines or azasu-gars) have been identified as an important class of therapeu-tic agents in the treatment of influenza infection,1cancermetastatis,2viral infections including AIDS,3and diabetes(Fig. 1).4As a result, numerous classes of inhibitors havebeen developed, some of which provide interesting insights into the mechanism of enzymatic glycoside hydrolysis.Amongst them, both naturally occurring and syntheticpolyhydroxylated piperidines5(1–4) have been shown tobe specific and potent inhibitors of glycosidases6and have been demonstrated to have great potential as drugs for treating a variety of carbohydrate mediated diseases.7 As a consequence of this, there has been a great deal of interest, not only in the synthesis of the natural products themselves, but also that of chemically modified analogues. However, most of the methodologies have been developed for the synthesis of compounds 1and4and their stereo-isomers,8,9which can be regarded as substituted piperidines,starting from the carbohydrates and, in general, require chiral starting materials to reach the specific target. Thus the development of new methods from achiral precursors for the enantioselective synthesis of polyhydroxylated piper-idines constitutes an area of current interest.10 Herein, we wish to report the complete asymmetric synthesis of1and4starting from readily available achiral 4-methyl phenacyl bromide5. |
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6楼2013-04-03 21:14:03
NearSecond
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2楼2013-04-02 15:54:24
3楼2013-04-02 17:13:47
NearSecond
金虫 (正式写手)
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4楼2013-04-02 17:53:25
