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首页> 外文期刊>Chemistry: A European journal >Directed Hydrogenations and an Ireland-Claisen Rearrangement Linked to Evans-Tishchenko Chemistry: The Highly Efficient Total Synthesis of the Marine Cyclodepsipeptide Doliculide
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Directed Hydrogenations and an Ireland-Claisen Rearrangement Linked to Evans-Tishchenko Chemistry: The Highly Efficient Total Synthesis of the Marine Cyclodepsipeptide Doliculide

机译：定向氢化和与Evans-Tishchenko化学相关的Ireland-Claisen重排：高效的海洋环十二烷基肽多立肽的全合成

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摘要

Two new convergent total syntheses have been developed for the cytotoxic, actin microfilament-stabilizing marine cyclodepsipeptide doliculide (1). A key strategic element of both routes is the establishment of the central stereogenic center of the characteristic polydeoxypropionate stereotriad by means of a hydroxyl-directed catalytic hydrogenation of a trisubstituted double bond. The requisite olefin substrates were obtained through a modified Suzuki-Miyaura coupling or through Ireland-Claisen rearrangement of a propionate ester, respectively; the latter was the direct result of a highly selective Evans-Tishchenko reduction of a hydroxy ketone that had been obtained in a stereoselective Paterson aldol reaction. Doliculide (1) was finally obtained in a total number of 17 or 15 (14) linear steps, respectively, which represents a substantial improvement over previous syntheses of this highly bioactive natural product.
机译：已经开发出两种新的收敛的总合成物，用于稳定细胞毒性，肌动蛋白微丝的海洋环二肽多立肽（1）。两种途径的关键战略要素是借助于羟基取代的三取代双键的催化氢化作用，建立特征性聚脱氧丙酸酯立体三联体的中心立体中心。所需的烯烃底物分别通过改良的Suzuki-Miyaura偶联或通过丙酸酯的Ireland-Claisen重排获得。后者是在立体选择性Paterson aldol反应中获得的高选择性Evans-Tishchenko还原羟基酮的直接结果。最后，分别以总共17或15（14）个线性步骤获得了多利舒利（1），这代表了对该高生物活性天然产物先前合成方法的实质性改进。

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