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Biocatalytic Strategies for the Asymmetric Synthesis of α-Hydroxy Ketones

机译:α-羟基酮不对称合成的生物催化策略

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摘要

Tnhe development of efficient syntheses for enantiomericallynenriched -hydroxy ketones is an important research focus in thenpharmaceutical industry. For example, -hydroxy ketones are foundnin antidepressants, in selective inhibitors of amyloid-u0001 protein pro-nduction (used in the treatment of Alzheimer’s), in farnesyl transferaseninhibitors (Kurasoin A and B), and in antitumor antibiotics (Olivomy-ncin A and Chromomycin A3). Moreover, -hydroxy ketones are of par-nticular value as fine chemicals because of their utility as buildingnblocks for the production of larger molecules. They can also be usednin preparing many other important structures, such as amino alco-nhols, diols, and so forth. Several purely chemical synthetic approachesnhave been proposed to afford these compounds, together with somenorganocatalytic strategies (thiazolium-based carboligations, prolinen-hydroxylations, and so forth). However, many of these chemicalnapproaches are not straightforward, lack selectivity, or are econom-nically unattractive because of the large number of chemical stepsnrequired (usually combined with low enantioselectivities).
机译:发展对映体富集的羟基酮的有效合成方法是当时制药业的重要研究重点。例如,β-羟基酮在抗抑郁药,淀粉样蛋白-u0001蛋白生产的选择性抑制剂(用于治疗阿尔茨海默氏病),法呢基转移酶抑制剂(库拉索因A和B)以及抗肿瘤抗生素(卵磷脂-ncin A和铬霉素A3)。此外,-羟基酮作为精细化学品具有特别的价值,因为它们可用作生产大分子的构建基块。它们也可用于制备许多其他重要结构,例如氨基醇,二醇等。已经提出了几种纯化学合成方法来提供这些化合物,以及一些有机催化策略(基于噻唑鎓的碳键合,脯氨酸-羟基化等)。然而,由于需要大量的化学步骤(通常与低对映选择性结合使用),许多这些化学方法并不简单,缺乏选择性或在经济上没有吸引力。

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  • 来源
    《Accounts of Chemical Research》 |2010年第2期|p.288-299|共12页
  • 作者单位

    Grupo de Biotransformaciones, Departamento de Quı ´mica Orga ´nica yFarmace ´utica, Facultad de Farmacia, Universidad Complutense de Madrid, Plazade Ramo ´n y Cajal, s. 28040 Madrid, Spain,‡Unidad de BiotransformacionesIndustriales, Parque Cientı ´fico de Madrid, PTM, C/ Santiago Grisolı ´a, 2, 28760 TresCantos, Madrid, Spain,§Dipartimento di Scienze e Tecnologie Alimentari eMicrobiologiche, Universita ` degli Studi di Milano, 20133 Milano, Italy,|Institute ofTechnical and Macromolecular Chemistry (ITMC), RWTH Aachen University,Worringerweg 1, D-52074 Aachen, Germany;

  • 收录信息 美国《科学引文索引》(SCI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
  • 原文格式 PDF
  • 正文语种 eng
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  • 入库时间 2022-08-17 13:24:23

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