Synthetic studies on the taxane skeleton: effective construction of eight-membered carbocyclic ring by palladium-catalyzed intramolecular α-alkenylation of a methyl ketone

Masayuki Utsugi; Yasuaki Kamada; Masahisa Nakada

doi:10.1016/j.tetlet.2008.05.105

Synthetic studies on the taxane skeleton: effective construction of eight-membered carbocyclic ring by palladium-catalyzed intramolecular α-alkenylation of a methyl ketone

Masayuki Utsugi, Yasuaki Kamada, 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

A new method for the construction of the eight-membered carbocyclic ring in the taxane skeleton is described. The palladium-catalyzed intramolecular α-alkenylation of a methyl ketone effectively constructed the eight-membered carbocyclic ring in the taxol model compound. To the best of our knowledge, this reaction is the first example of forming an eight-membered carbocyclic ring by the palladium-catalyzed intramolecular α-alkenylation of a ketone.

Original language	English
Pages (from-to)	4754-4757
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	32
DOIs	https://doi.org/10.1016/j.tetlet.2008.05.105
Publication status	Published - 2008 Aug 4

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.05.105

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title = "Synthetic studies on the taxane skeleton: effective construction of eight-membered carbocyclic ring by palladium-catalyzed intramolecular α-alkenylation of a methyl ketone",

abstract = "A new method for the construction of the eight-membered carbocyclic ring in the taxane skeleton is described. The palladium-catalyzed intramolecular α-alkenylation of a methyl ketone effectively constructed the eight-membered carbocyclic ring in the taxol model compound. To the best of our knowledge, this reaction is the first example of forming an eight-membered carbocyclic ring by the palladium-catalyzed intramolecular α-alkenylation of a ketone.",

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

note = "Funding Information: This work was financially supported in part by a Waseda University Grant for Special Research Projects, a Grant-in-Aid for Scientific Research (B), (C), and Scientific Research on Priority Areas (Creation of Biologically Functional Molecules (No. 17035082)), and the Global COE program {\textquoteleft}Center for Practical Chemical Wisdom{\textquoteright} by MEXT. ",

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T1 - Synthetic studies on the taxane skeleton

T2 - effective construction of eight-membered carbocyclic ring by palladium-catalyzed intramolecular α-alkenylation of a methyl ketone

AU - Utsugi, Masayuki

AU - Kamada, Yasuaki

AU - Nakada, Masahisa

N1 - Funding Information: This work was financially supported in part by a Waseda University Grant for Special Research Projects, a Grant-in-Aid for Scientific Research (B), (C), and Scientific Research on Priority Areas (Creation of Biologically Functional Molecules (No. 17035082)), and the Global COE program ‘Center for Practical Chemical Wisdom’ by MEXT.

PY - 2008/8/4

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N2 - A new method for the construction of the eight-membered carbocyclic ring in the taxane skeleton is described. The palladium-catalyzed intramolecular α-alkenylation of a methyl ketone effectively constructed the eight-membered carbocyclic ring in the taxol model compound. To the best of our knowledge, this reaction is the first example of forming an eight-membered carbocyclic ring by the palladium-catalyzed intramolecular α-alkenylation of a ketone.

AB - A new method for the construction of the eight-membered carbocyclic ring in the taxane skeleton is described. The palladium-catalyzed intramolecular α-alkenylation of a methyl ketone effectively constructed the eight-membered carbocyclic ring in the taxol model compound. To the best of our knowledge, this reaction is the first example of forming an eight-membered carbocyclic ring by the palladium-catalyzed intramolecular α-alkenylation of a ketone.

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Synthetic studies on the taxane skeleton: effective construction of eight-membered carbocyclic ring by palladium-catalyzed intramolecular α-alkenylation of a methyl ketone

Abstract

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