Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI<inf>2</inf>-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 Satou, Noritaka Chida

Research output: Contribution to journal › Article

11 Citations (Scopus)

Abstract

A convergent synthesis of the ABC ring of antitumor natural product paclitaxel (Taxol) is described. SmI<inf>2</inf>-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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Cyclization
Paclitaxel
aldehydes
rings
Benzoates
synthesis
products
Biological Products
Aldehydes
d-glucal
1,3-cyclohexanedione

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI<inf>2</inf>-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; Satou, Takaaki; Chida, Noritaka.

In: Organic Letters, Vol. 17, No. 11, 05.06.2015, p. 2570-2573.

Research output: Contribution to journal › Article

Fukaya, K, Tanaka, Y, Sato, AC, Kodama, K, Yamazaki, H, Ishimoto, T, Nozaki, Y, Iwaki, YM, Yuki, Y, Umei, K, Sugai, T, Yamaguchi, Y, Watanabe, A, Oishi, T, Satou, T & Chida, N 2015, 'Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI<inf>2</inf>-mediated cyclization', Organic Letters, vol. 17, no. 11, pp. 2570-2573. https://doi.org/10.1021/acs.orglett.5b01173
Fukaya K, Tanaka Y, Sato AC, Kodama K, Yamazaki H, Ishimoto T et al. Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI<inf>2</inf>-mediated cyclization. Organic Letters. 2015 Jun 5;17(11):2570-2573. https://doi.org/10.1021/acs.orglett.5b01173
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 ; Satou, Takaaki ; Chida, Noritaka. / Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI<inf>2</inf>-mediated cyclization. In: Organic Letters. 2015 ; Vol. 17, No. 11. pp. 2570-2573.
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AU - Yamazaki, Hirohisa

AU - Ishimoto, Takeru

AU - Nozaki, Yasuyoshi

AU - Iwaki, Yuki M.

AU - Yuki, Yohei

AU - Umei, Kentaro

AU - Sugai, Tomoya

AU - Yamaguchi, Yu

AU - Watanabe, Ami

AU - Oishi, Takeshi

AU - Satou, Takaaki

AU - Chida, Noritaka

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