Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki-Miyaura coupling reaction

Masayuki Utsugi; Yasuaki Kamada; Hidetoshi Miyamoto; Masahisa Nakada

doi:10.1016/j.tetlet.2007.07.179

Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki-Miyaura coupling reaction

Masayuki Utsugi, Yasuaki Kamada, Hidetoshi Miyamoto, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

15 Citations (Scopus)

Abstract

Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki-Miyaura coupling reaction is described. A conjugate addition of cyanide to enone 17 proceeded diastereoselectively to provide the desired 18 incorporating the correct C3 stereogenic center in the taxol C-ring. The intramolecular B-alkyl Suzuki-Miyaura coupling reaction of 22, which was derived from 18, successfully furnished the taxol B-ring in 81% yield.

Original language	English
Pages (from-to)	6868-6872
Number of pages	5
Journal	Tetrahedron Letters
Volume	48
Issue number	39
DOIs	https://doi.org/10.1016/j.tetlet.2007.07.179
Publication status	Published - 2007 Sept 24

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.07.179

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title = "Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki-Miyaura coupling reaction",

abstract = "Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki-Miyaura coupling reaction is described. A conjugate addition of cyanide to enone 17 proceeded diastereoselectively to provide the desired 18 incorporating the correct C3 stereogenic center in the taxol C-ring. The intramolecular B-alkyl Suzuki-Miyaura coupling reaction of 22, which was derived from 18, successfully furnished the taxol B-ring in 81% yield.",

author = "Masayuki Utsugi and Yasuaki Kamada and Hidetoshi Miyamoto and Masahisa Nakada",

note = "Funding Information: This work was financially supported in part by a Waseda University Grant for Special Research Projects and a Grant-in-Aid for Scientific Research (C) and Scientific Research on Priority Areas (Creation of Biologically Functional Molecules (No. 17035082)) from MEXT, Japan. We are also indebted to GCOE {\textquoteleft}Practical Chemical Wisdom{\textquoteright}. ",

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doi = "10.1016/j.tetlet.2007.07.179",

language = "English",

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T1 - Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki-Miyaura coupling reaction

AU - Utsugi, Masayuki

AU - Kamada, Yasuaki

AU - Miyamoto, Hidetoshi

AU - Nakada, Masahisa

N1 - Funding Information: This work was financially supported in part by a Waseda University Grant for Special Research Projects and a Grant-in-Aid for Scientific Research (C) and Scientific Research on Priority Areas (Creation of Biologically Functional Molecules (No. 17035082)) from MEXT, Japan. We are also indebted to GCOE ‘Practical Chemical Wisdom’.

PY - 2007/9/24

Y1 - 2007/9/24

N2 - Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki-Miyaura coupling reaction is described. A conjugate addition of cyanide to enone 17 proceeded diastereoselectively to provide the desired 18 incorporating the correct C3 stereogenic center in the taxol C-ring. The intramolecular B-alkyl Suzuki-Miyaura coupling reaction of 22, which was derived from 18, successfully furnished the taxol B-ring in 81% yield.

AB - Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki-Miyaura coupling reaction is described. A conjugate addition of cyanide to enone 17 proceeded diastereoselectively to provide the desired 18 incorporating the correct C3 stereogenic center in the taxol C-ring. The intramolecular B-alkyl Suzuki-Miyaura coupling reaction of 22, which was derived from 18, successfully furnished the taxol B-ring in 81% yield.

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DO - 10.1016/j.tetlet.2007.07.179

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Construction of the taxane skeleton via the stereoselective conjugate addition of cyanide and the intramolecular B-alkyl Suzuki-Miyaura coupling reaction

Abstract

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