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

…, HJ Gais, K Cheng, C Vermeeren

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

Full Text: HTML

Citation Number: 33

Abstract

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 ...