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首页> 外文期刊>Chemistry: A European journal >A Highly Stereoselective and Flexible Strategy for the Convergent Synthesis of Long-Chain Polydeoxypropionates: Application towards the Synthesis of the Glycolipid Membrane Components Hydroxyphthioceranic and Phthioceranic Acid
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A Highly Stereoselective and Flexible Strategy for the Convergent Synthesis of Long-Chain Polydeoxypropionates: Application towards the Synthesis of the Glycolipid Membrane Components Hydroxyphthioceranic and Phthioceranic Acid

机译：聚合的长链聚脱氧丙酸酯的高度立体选择性和灵活的策略：在糖脂膜成分羟硫代天竺葵和苯硫代天冬氨酸的合成中的应用

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摘要

A highly stereocontrolled and flexible access to biologically relevant polydeoxypropionates in optically pure form has been developed. Taking advantage of our previously established strategy for the asymmetric and stereodivergent synthesis of trideoxypropionate building blocks, we have now been able to assemble large polydeoxypropionate chains with defined configuration in a highly convergent manner. Central steps of this approach include two Suzuki-Miyaura cross-coupling reactions with subsequent highly diastereoselective hydrogenations to join three advanced synthetic intermediates in excellent yield and with full stereochemical control. We have applied this strategy successfully towards the asymmetric synthesis of glycolipid membrane components phthioceranic acid and hydroxy-phthioceranic acid, the latter of which was synthesized on a half-gram scale.
机译：已经开发了高度立体可控且灵活地获得光学纯形式的生物学上相关的聚脱氧丙酸酯的方法。利用我们先前建立的不对称和立体发散的三脱氧丙酸酯结构单元合成策略，我们现在能够以高度收敛的方式组装具有确定构型的大型聚脱氧丙酸酯链。该方法的主要步骤包括两个Suzuki-Miyaura交叉偶联反应，以及随后的高度非对映选择性加氢，以优异的产率和完全的立体化学控制将三个先进的合成中间体连接在一起。我们已经成功地将这种策略应用于糖脂膜成分苯硫醚酸和羟基苯硫醚酸的不对称合成，后者以半克规模合成。

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