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

doi:10.1021/acs.orglett.5b01174

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

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

43 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	2574-2577
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.5b01174
Publication status	Published - 2015 Jun 5

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "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.",

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T1 - Synthesis of paclitaxel. 2. construction of the ABCD ring and formal synthesis

AU - Fukaya, Keisuke

AU - Kodama, Keisuke

AU - Tanaka, Yuta

AU - Yamazaki, Hirohisa

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 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.

AB - 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.

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

Abstract

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