Total Synthesis of Paclitaxel

Shota Iiyama; Keisuke Fukaya; Yu Yamaguchi; Ami Watanabe; Hiroaki Yamamoto; Shota Mochizuki; Ryosuke Saio; Takashi Noguchi; Takeshi Oishi; Takaaki Sato; Noritaka Chida

doi:10.1021/acs.orglett.1c03851

Total Synthesis of Paclitaxel

Shota Iiyama, Keisuke Fukaya, Yu Yamaguchi, Ami Watanabe, Hiroaki Yamamoto, Shota Mochizuki, Ryosuke Saio, Takashi Noguchi, Takeshi Oishi, Takaaki Sato, Noritaka Chida

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

10 Citations (Scopus)

Abstract

The total synthesis of paclitaxel (Taxol) is described. Double Rubottom oxidation of the bis(silyl enol ether) derived from a tricarbocyclic diketone effectively installed a bridgehead olefin and C-5/C-13 hydroxy groups in a one-step operation. The novel Ag-promoted oxetane formation smoothly constructed the tetracyclic framework of paclitaxel.

Original language	English
Pages (from-to)	202-206
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.1c03851
Publication status	Published - 2022 Jan 14

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.1c03851

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title = "Total Synthesis of Paclitaxel",

abstract = "The total synthesis of paclitaxel (Taxol) is described. Double Rubottom oxidation of the bis(silyl enol ether) derived from a tricarbocyclic diketone effectively installed a bridgehead olefin and C-5/C-13 hydroxy groups in a one-step operation. The novel Ag-promoted oxetane formation smoothly constructed the tetracyclic framework of paclitaxel.",

author = "Shota Iiyama and Keisuke Fukaya and Yu Yamaguchi and Ami Watanabe and Hiroaki Yamamoto and Shota Mochizuki and Ryosuke Saio and Takashi Noguchi and Takeshi Oishi and Takaaki Sato and Noritaka Chida",

note = "Funding Information: This work was supported by a Grant-in Aid for Scientific Research (B) from JSPS (26288018). Publisher Copyright: {\textcopyright} 2021 American Chemical Society",

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doi = "10.1021/acs.orglett.1c03851",

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T1 - Total Synthesis of Paclitaxel

AU - Iiyama, Shota

AU - Fukaya, Keisuke

AU - Yamaguchi, Yu

AU - Watanabe, Ami

AU - Yamamoto, Hiroaki

AU - Mochizuki, Shota

AU - Saio, Ryosuke

AU - Noguchi, Takashi

AU - Oishi, Takeshi

AU - Sato, Takaaki

AU - Chida, Noritaka

PY - 2022/1/14

Y1 - 2022/1/14

N2 - The total synthesis of paclitaxel (Taxol) is described. Double Rubottom oxidation of the bis(silyl enol ether) derived from a tricarbocyclic diketone effectively installed a bridgehead olefin and C-5/C-13 hydroxy groups in a one-step operation. The novel Ag-promoted oxetane formation smoothly constructed the tetracyclic framework of paclitaxel.

AB - The total synthesis of paclitaxel (Taxol) is described. Double Rubottom oxidation of the bis(silyl enol ether) derived from a tricarbocyclic diketone effectively installed a bridgehead olefin and C-5/C-13 hydroxy groups in a one-step operation. The novel Ag-promoted oxetane formation smoothly constructed the tetracyclic framework of paclitaxel.

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EP - 206

JO - Organic Letters

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Total Synthesis of Paclitaxel

Abstract

ASJC Scopus subject areas

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