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NearSecond

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专业: 肿瘤研究体系新技术

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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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1楼 2013-04-02 14:35:32

已阅回复此楼关注TA 给TA发消息送TA红花 TA的回帖

ty1255212249

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【答案】应助回帖

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NearSecond: 金币+10, 翻译EPI+1, ★★★很有帮助, 谢谢您，您是直接谷歌翻译粘过来的吧，我就是这样翻译的，不过不好使。但是依然很谢谢您，辛苦了。 2013-04-04 07:28:11

取代的哌啶的不对称合成已经described.b-cyclodextrin或恶唑硼烷催化的不对称还原一个叠氮基芳基酮为相应的醇已被作为关键步随着关环复分解反应和选择性羟化。

取代的哌啶（多羟基哌啶或azasu雀鳝）已被确定为一类重要的药物治疗抽动在流感病毒感染，治疗1cancermetastatis 2viral感染，包括艾滋病，和糖尿病（图1）4。结果，许多类抑制剂被开发，其中一些提供酶糖苷水解机理的有趣的见解。其中，自然发生和syntheticpolyhydroxylated piperidines5（1–4）已被证明是具体和有效的抑制剂glycosidases6and已被证明有很大的潜力，作为药物治疗多种碳水化合物介导的疾病。7

因此，有极大的兴趣，不仅在天然产物合成自己，而且，化学改性的类似物。然而，大多数的方法已被开发用于化合物的合成1and4and其立体异构体，8,9which可以被视为取代的哌啶，从碳水化合物，在一般情况下，要求

手性原料达到特定的目标。从而为多羟基Piper idines的不对称合成手性前体的新方法的发展是当前interest.10面积外，我们

要报告的完整的不对称合成的手性4-甲基苯甲酰甲基of1and4starting现成bromide5。