title: Practical synthesis of the C-ring precursor of paclitaxel from 3-methoxytoluene.
abstract: 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.
authors: Department of Applied Chemistry, Keio University, Yokohama, Japan.
authors: Keisuke
authors: K
authors: Fukaya
authors: Department of Applied Chemistry, Keio University, Yokohama, Japan.
authors: Yu
authors: Y
authors: Yamaguchi
authors: Department of Applied Chemistry, Keio University, Yokohama, Japan.
authors: Ami
authors: A
authors: Watanabe
authors: Department of Applied Chemistry, Keio University, Yokohama, Japan.
authors: Hiroaki
authors: H
authors: Yamamoto
authors: Department of Applied Chemistry, Keio University, Yokohama, Japan.
authors: Tomoya
authors: T
authors: Sugai
authors: Department of Pharmaceutical Science, Keio University, Tokyo, Japan.
authors: Takeshi
authors: T
authors: Sugai
authors: Department of Applied Chemistry, Keio University, Yokohama, Japan.
authors: Takaaki
authors: T
authors: Sato
authors: Department of Applied Chemistry, Keio University, Yokohama, Japan.
authors: Noritaka
authors: N
authors: Chida
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis*; D003510:Cyclohexanes / Q000737:chemistry; D005557:Formaldehyde / Q000737:chemistry; D008049:Lipase / Q000737:chemistry; D017239:Paclitaxel / Q000138:chemical synthesis*; D014050:Toluene / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D003510:Cyclohexanes; D005557:Formaldehyde; D014050:Toluene; D008049:Lipase; D017239:Paclitaxel; C000614356:3-methoxytoluene