title: Synthesis of Paclitaxel. 1. Synthesis of the ABC Ring of Paclitaxel by SmI2-Mediated Cyclization.
abstract: 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.
authors.affiliation: †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Keisuke
authors.initials: K
authors.lastname: Fukaya
authors.affiliation: †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Yuta
authors.initials: Y
authors.lastname: Tanaka
authors.affiliation: †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Ayako C
authors.initials: AC
authors.lastname: Sato
authors.affiliation: †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Keisuke
authors.initials: K
authors.lastname: Kodama
authors.affiliation: †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Hirohisa
authors.initials: H
authors.lastname: Yamazaki
authors.affiliation: †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Takeru
authors.initials: T
authors.lastname: Ishimoto
authors.affiliation: †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Yasuyoshi
authors.initials: Y
authors.lastname: Nozaki
authors.affiliation: †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Yuki M
authors.initials: YM
authors.lastname: Iwaki
authors.affiliation: †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Yohei
authors.initials: Y
authors.lastname: Yuki
authors.affiliation: †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Kentaro
authors.initials: K
authors.lastname: Umei
authors.affiliation: †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Tomoya
authors.initials: T
authors.lastname: Sugai
authors.affiliation: †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Yu
authors.initials: Y
authors.lastname: Yamaguchi
authors.affiliation: †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Ami
authors.initials: A
authors.lastname: Watanabe
authors.affiliation: ‡School of Medicine, Keio University, 4-1-1 Hiyoshi, Kohoku-ku, Yokohama 223-8521, Japan.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Oishi
authors.affiliation: †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Takaaki
authors.initials: T
authors.lastname: Sato
authors.affiliation: †Department Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Noritaka
authors.initials: N
authors.lastname: Chida
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008968:Molecular Conformation; D017239:Paclitaxel / Q000138:chemical synthesis* / Q000737:chemistry; D011506:Proteins / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D011506:Proteins; C080380:sperm motility inhibitor 2; D017239:Paclitaxel