815577-89-0Relevant 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.
Synthetic studies on the taxane skeleton: Construction of eight-membered carbocyclic rings by the intramolecular B-alkyl Suzuki-Miyaura cross-coupling reaction
Kawada, Hatsuo,Iwamoto, Mitsuhiro,Utsugi, Masayuki,Miyano, Masayuki,Nakada, Masahisa
, p. 4491 - 4494 (2007/10/03)
(Chemical equation presented) Construction of eight-membered carbocyclic rings via the intramolecular B-alkyl Suzuki-Miyaura cross-coupling reaction has been studied. This protocol proved its potency through the formation of the eight-membered ring posses
