954096-33-4Relevant academic research and scientific papers
Formal total synthesis of (-)-taxol through Pd-catalyzed eight-membered carbocyclic ring formation
Hirai, Sho,Utsugi, Masayuki,Iwamoto, Mitsuhiro,Nakada, Masahisa
, p. 355 - 359 (2015/02/19)
A formal total synthesis of (-)-taxol by a convergent approach utilizing Pd-catalyzed intramolecular alkenylation is described. Formation of the eight-membered carbocyclic ring has been a problem in the convergent total synthesis of taxol but it was solved by the Pd-catalyzed intramolecular alkenylation of a methyl ketone affording the cyclized product in excellent yield (97 %), indicating the high efficiency of the Pd-catalyzed intramolecular alkenylation. Rearrangement of the epoxy benzyl ether through a 1,5-hydride shift, generating the C3 stereogenic center and subsequently forming the C1-C2 benzylidene, was discovered and utilized in the preparation of a substrate for the Pd-catalyzed reaction.
Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki-Miyaura coupling reaction
Utsugi, Masayuki,Kamada, Yasuaki,Miyamoto, Hidetoshi,Nakada, Masahisa
, p. 6868 - 6872 (2008/02/12)
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 t
