Synthesis of paclitaxel. 2. construction of the ABCD ring and formal synthesis

Keisuke Fukaya, Keisuke Kodama, Yuta Tanaka, Hirohisa Yamazaki, Tomoya Sugai, Yu Yamaguchi, Ami Watanabe, Takeshi Oishi, Takaaki Sato, Noritaka Chida

研究成果: Article査読

33 被引用数 (Scopus)

抄録

A formal synthesis of the antitumor diterpenoid paclitaxel (Taxol) is described. The ABC ring of paclitaxel, synthesized starting from 1,3-cyclohexanedione and tri-O-acetyl-d-glucal by SmI2-mediated cyclization as the key transformation, was successfully converted to Takahashi's tetracyclic oxetane intermediate. A double Chugaev reaction was employed for introduction of the strained bridgehead olefin, and stereoselective formation of the oxetane ring afforded the known synthetic intermediate, completing the formal synthesis of paclitaxel.

本文言語English
ページ(範囲)2574-2577
ページ数4
ジャーナルOrganic Letters
17
11
DOI
出版ステータスPublished - 2015 6月 5

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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