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NearSecond金蟲 (正式寫手)
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[求助]
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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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NearSecond
金蟲 (正式寫手)
- 應(yīng)助: 3 (幼兒園)
- 金幣: 1797.6
- 散金: 27
- 紅花: 1
- 帖子: 602
- 在線: 207.1小時
- 蟲號: 1834342
- 注冊: 2012-05-25
- 專業(yè): 腫瘤研究體系新技術(shù)
4樓2013-04-02 17:53:25
NearSecond
金蟲 (正式寫手)
- 應(yīng)助: 3 (幼兒園)
- 金幣: 1797.6
- 散金: 27
- 紅花: 1
- 帖子: 602
- 在線: 207.1小時
- 蟲號: 1834342
- 注冊: 2012-05-25
- 專業(yè): 腫瘤研究體系新技術(shù)
2樓2013-04-02 15:54:24
3樓2013-04-02 17:13:47
【答案】應(yīng)助回帖
★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ★ ...
NearSecond: 金幣+70, ★★★★★最佳答案, 謝謝您，分給別人了一點，您沒意見吧，都不容易。非常感謝。 2013-04-04 07:31:55
NearSecond: 金幣+70, ★★★★★最佳答案, 謝謝您，分給別人了一點，您沒意見吧，都不容易。非常感謝。 2013-04-04 07:31:55
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我們已經(jīng)描述過不對稱合成的取代哌啶的方法.b-環(huán)糊精或惡唑硼烷催化的不對稱還原OFA-疊氮芳基酮為相應(yīng)的醇已經(jīng)被證明為關(guān)鍵步驟，伴隨著閉環(huán)復(fù)分解反應(yīng)和選擇性雙羥基化反應(yīng)。 取代的哌啶（羥基哌啶或）已被確定為在在流感病毒感染、轉(zhuǎn)移癌、病毒感染包括艾滋病在內(nèi)和糖尿�。▓D1）的一類重要的治療藥物，因此，很多抑制劑都被開發(fā)了，其中一些在對酶促糖苷水解反應(yīng)機制上產(chǎn)生很大興趣.在這些藥物當中，無論是天然存在的還是合成的多羥基哌啶都已展示出明確的作用效果是很強的糖苷酶抑制劑，并被證明有很大的潛力成為治療多種碳水化合物介導(dǎo)的疾病的藥物。 因此，不僅在合成的天然化合物本身，在化學(xué)修飾的類似物合成上也具有極大的興趣。然而，大多數(shù)已被開發(fā)的方法都是用來合成被稱為取代哌啶的化合物1和4and它們的立體異構(gòu)體8和9，它們從碳水化合物開始并在一般情況中，需要手性起始物來達到的特定目的。因此，從非手性前體物質(zhì)具有立體選擇性的合成多羥基哌啶事當前我們應(yīng)當發(fā)展的方向.在此，我們希望報導(dǎo)出從容易獲得的非手性4 - 甲基苯甲酰溴化物來不對稱合成化合物1和4的方法。 |
5樓2013-04-03 16:40:16
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