Tetrahedron Letters

Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki–Miyaura coupling reaction

M Utsugi, Y Kamada, H Miyamoto, M Nakada

Index: Utsugi, Masayuki; Kamada, Yasuaki; Miyamoto, Hidetoshi; Nakada, Masahisa Tetrahedron Letters, 2007 , vol. 48, # 39 p. 6868 - 6872

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Citation Number: 12

Abstract

Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki–Miyaura coupling reaction is described. A conjugate addition of cyanide to enone 17 proceeded diastereoselectively to provide the desired 18 incorporating the correct C3 stereogenic center in the taxol C-ring. The intramolecular B- alkyl Suzuki–Miyaura coupling reaction of 22, which was derived from 18, successfully ...