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

doi:10.1021/acs.orglett.5b01173

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

研究成果: Article › 査読

20 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	2570-2573
ページ数	4
ジャーナル	Organic Letters
巻	17
号	11
DOI	https://doi.org/10.1021/acs.orglett.5b01173
出版ステータス	Published - 2015 6 5

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

文献へのアクセス

10.1021/acs.orglett.5b01173

フィンガープリント「Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI<sub>2</sub>-mediated cyclization」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

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

Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI₂-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 ; Sato, Takaaki ; Chida, Noritaka.

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

研究成果: Article › 査読

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 , Sato, T & Chida, N 2015, 'Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI₂-mediated cyclization', Organic Letters, vol. 17, no. 11, pp. 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 ; Sato, Takaaki ; Chida, Noritaka. / Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI₂-mediated cyclization. In: Organic Letters. 2015 ; Vol. 17, No. 11. pp. 2570-2573.

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AU - Ishimoto, Takeru

AU - Nozaki, Yasuyoshi

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AU - Umei, Kentaro

AU - Sugai, Tomoya

AU - Yamaguchi, Yu

AU - Watanabe, Ami

AU - Oishi, Takeshi

AU - Sato, Takaaki

AU - Chida, Noritaka

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