Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI2-mediated cyclization

Keisuke Fukaya, Yuta Tanaka, Ayako C. Sato, Keisuke Kodama, Hirohisa Yamazaki, Takeru Ishimoto, Yasuyoshi Nozaki, Yuki M. Iwaki, Yohei Yuki, Kentaro Umei, Tomoya Sugai, Yu Yamaguchi, Ami Watanabe, Takeshi Oishi, Takaaki Sato, Noritaka Chida

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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.

Original languageEnglish
Pages (from-to)2570-2573
Number of pages4
JournalOrganic Letters
Volume17
Issue number11
DOIs
Publication statusPublished - 2015 Jun 5

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Fukaya, K., Tanaka, Y., Sato, A. C., Kodama, K., Yamazaki, H., Ishimoto, T., Nozaki, Y., Iwaki, Y. M., Yuki, Y., Umei, K., Sugai, T., Yamaguchi, Y., Watanabe, A., Oishi, T., Sato, T., & Chida, N. (2015). Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI2-mediated cyclization. Organic Letters, 17(11), 2570-2573. https://doi.org/10.1021/acs.orglett.5b01173