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Asymmetric synthesis of the highly potent anti-metastatic prostacyclin analogue cicaprost and its isomer isocicaprost

…, HJ Gais, K Cheng, C Vermeeren

文献索引:Lerm, Marco; Gais, Hans-Joachim; Cheng, Kejun; Vermeeren, Cornelia Journal of the American Chemical Society, 2003 , vol. 125, # 32 p. 9653 - 9667

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被引用次数: 33

摘要

An asymmetric synthesis of the anti-metastatic prostacyclin analogue cicaprost and a formal one of its isomer isocicaprost by a new route are described. A key step of these syntheses is the coupling of a chiral bicyclic C6-C14 ethynyl building block with a chiral C15-C21 ω-side chain amide building block with formation of the C14-C15 bond of the target molecules. A highly stereoselective reduction of the thereby obtained C6-C21 intermediate carrying a ...