326922-35-4Relevant academic research and scientific papers
Practical synthesis of the C-ring precursor of paclitaxel from 3-methoxytoluene
Fukaya, Keisuke,Yamaguchi, Yu,Watanabe, Ami,Yamamoto, Hiroaki,Sugai, Tomoya,Sugai, Takeshi,Sato, Takaaki,Chida, Noritaka
, p. 273 - 279 (2016/05/09)
The practical synthesis of the C-ring precursor of paclitaxel starting from 3-methoxytoluene is described. Lipase-catalyzed kinetic resolution of a substituted cyclohexane-1,2-diol, derived from 3-methoxytoluene in three steps, successfully afforded a desired enantiomer with >99% ee, which was transformed to a cyclohexenone. 1,4-Addition of a vinyl metal species, followed by Mukaiyama aldol reaction with formalin in the presence of a Lewis acid provided the known C-ring precursor of paclitaxel in a 10 g scale.
Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI2-mediated cyclization
Fukaya, Keisuke,Tanaka, Yuta,Sato, Ayako C.,Kodama, Keisuke,Yamazaki, Hirohisa,Ishimoto, Takeru,Nozaki, Yasuyoshi,Iwaki, Yuki M.,Yuki, Yohei,Umei, Kentaro,Sugai, Tomoya,Yamaguchi, Yu,Watanabe, Ami,Oishi, Takeshi,Sato, Takaaki,Chida, Noritaka
, p. 2570 - 2573 (2015/06/16)
A convergent synthesis of the ABC ring of antitumor natural product paclitaxel (Taxol) is described. SmI2-mediated reductive cyclization of an allylic benzoate possessing an aldehyde function, synthesized from tri-O-acetyl-d-glucal and 1,3-cyclohexanedione, smoothly afforded the highly strained 6-8-6 tricarbocyclic structure in 66% yield.
Chiral synthesis of the CD ring unit of paclitaxel from D-glucal
Momose,Setoguchi,Fujita,Tamura,Chida
, p. 2237 - 2238 (2007/10/03)
The chiral synthesis of the fully functionalized CD ring unit of paclitaxel 3 is described; the three component coupling reaction of a cyclohexenone derived from D-glucal by way of Ferrier's carbocyclization with vinyl cuprate and formal-dehyde effectivel
