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

Research output: Contribution to journal › Article › peer-review

36 Citations (Scopus)

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 language	English
Pages (from-to)	2570-2573
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.5b01173
Publication status	Published - 2015 Jun 5

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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

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

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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.",

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

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doi = "10.1021/acs.orglett.5b01173",

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T1 - Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI2-mediated cyclization

AU - Fukaya, Keisuke

AU - Tanaka, Yuta

AU - Sato, Ayako C.

AU - Kodama, Keisuke

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 - Sato, Takaaki

AU - Chida, Noritaka

PY - 2015/6/5

Y1 - 2015/6/5

N2 - 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.

AB - 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.

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

Abstract

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