Synthesis of the AC ring of paclitaxel: Formation of the C ring by [3+2] cycloaddition with a preformed A ring

Kazuoki Nakai; Takayuki Doi; Takashi Takahashi

doi:10.1055/s-2005-863739

Synthesis of the AC ring of paclitaxel: Formation of the C ring by [3+2] cycloaddition with a preformed A ring

Kazuoki Nakai, Takayuki Doi, Takashi Takahashi

PHA - Molecular Pharmaceutical Science

Tokyo Institute of Technology

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

7 Citations (Scopus)

Abstract

The stereoselective formation of the C ring was accomplished by nitrile oxide [3+2] cycloaddition of an intermediate with the A ring already constructed. We found that stereoelectronic effect to a 1,1-substituted alkene moiety is important in the reaction.

Original language	English
Pages (from-to)	866-868
Number of pages	3
Journal	Synlett
Issue number	5
DOIs	https://doi.org/10.1055/s-2005-863739
Publication status	Published - 2005 Mar 21

Keywords

Cycloadditions
Nitrile oxide
Paclitaxel

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10.1055/s-2005-863739

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title = "Synthesis of the AC ring of paclitaxel: Formation of the C ring by [3+2] cycloaddition with a preformed A ring",

abstract = "The stereoselective formation of the C ring was accomplished by nitrile oxide [3+2] cycloaddition of an intermediate with the A ring already constructed. We found that stereoelectronic effect to a 1,1-substituted alkene moiety is important in the reaction.",

keywords = "Cycloadditions, Nitrile oxide, Paclitaxel",

author = "Kazuoki Nakai and Takayuki Doi and Takashi Takahashi",

year = "2005",

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AU - Nakai, Kazuoki

AU - Doi, Takayuki

AU - Takahashi, Takashi

PY - 2005/3/21

Y1 - 2005/3/21

N2 - The stereoselective formation of the C ring was accomplished by nitrile oxide [3+2] cycloaddition of an intermediate with the A ring already constructed. We found that stereoelectronic effect to a 1,1-substituted alkene moiety is important in the reaction.

AB - The stereoselective formation of the C ring was accomplished by nitrile oxide [3+2] cycloaddition of an intermediate with the A ring already constructed. We found that stereoelectronic effect to a 1,1-substituted alkene moiety is important in the reaction.

KW - Cycloadditions

KW - Nitrile oxide

KW - Paclitaxel

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ER -

Synthesis of the AC ring of paclitaxel: Formation of the C ring by [3+2] cycloaddition with a preformed A ring

Abstract

Keywords

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