Development of silicon-tethered anionic reaction and its application to the synthesis of chiral A-ring moieties of Taxol™

Mitsuhiro Iwamoto; Masayuki Miyano; Masayuki Utsugi; Hatsuo Kawada; Masahisa Nakada

doi:10.1016/j.tetlet.2004.09.143

Development of silicon-tethered anionic reaction and its application to the synthesis of chiral A-ring moieties of Taxol™

Mitsuhiro Iwamoto, Masayuki Miyano, Masayuki Utsugi, Hatsuo Kawada, Masahisa Nakada

School of Advanced Science and Engineering

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

18 Citations (Scopus)

Abstract

Silicon-tethered intramolecular nucleophilic additions of a hydroxymethyl unit to ketones in β-hydroxyketones have been developed. The product obtained by this protocol was successfully converted to chiral A-ring moieties of Taxol™. Also developed was a promising silicon-tethered intramolecular α-alkylation reaction of the cyclic hydroxyketone.

Original language	English
Pages (from-to)	8647-8651
Number of pages	5
Journal	Tetrahedron Letters
Volume	45
Issue number	47
DOIs	https://doi.org/10.1016/j.tetlet.2004.09.143
Publication status	Published - 2004 Nov 15

Keywords

Alkylation
Carbanion
Intramolecular reaction
Nucleophilic addition
Silicon tethered
Taxol™

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.09.143

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title = "Development of silicon-tethered anionic reaction and its application to the synthesis of chiral A-ring moieties of Taxol{\texttrademark}",

abstract = "Silicon-tethered intramolecular nucleophilic additions of a hydroxymethyl unit to ketones in β-hydroxyketones have been developed. The product obtained by this protocol was successfully converted to chiral A-ring moieties of Taxol{\texttrademark}. Also developed was a promising silicon-tethered intramolecular α-alkylation reaction of the cyclic hydroxyketone.",

keywords = "Alkylation, Carbanion, Intramolecular reaction, Nucleophilic addition, Silicon tethered, Taxol{\texttrademark}",

author = "Mitsuhiro Iwamoto and Masayuki Miyano and Masayuki Utsugi and Hatsuo Kawada and Masahisa Nakada",

note = "Funding Information: This work was financially supported in part by Waseda University Grant for Special Research Projects. We are also indebted to 21COE {\textquoteleft}Practical Nano-Chemistry{\textquoteright}. ",

year = "2004",

month = nov,

day = "15",

doi = "10.1016/j.tetlet.2004.09.143",

language = "English",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Development of silicon-tethered anionic reaction and its application to the synthesis of chiral A-ring moieties of Taxol™

AU - Iwamoto, Mitsuhiro

AU - Miyano, Masayuki

AU - Utsugi, Masayuki

AU - Kawada, Hatsuo

AU - Nakada, Masahisa

N1 - Funding Information: This work was financially supported in part by Waseda University Grant for Special Research Projects. We are also indebted to 21COE ‘Practical Nano-Chemistry’.

PY - 2004/11/15

Y1 - 2004/11/15

N2 - Silicon-tethered intramolecular nucleophilic additions of a hydroxymethyl unit to ketones in β-hydroxyketones have been developed. The product obtained by this protocol was successfully converted to chiral A-ring moieties of Taxol™. Also developed was a promising silicon-tethered intramolecular α-alkylation reaction of the cyclic hydroxyketone.

AB - Silicon-tethered intramolecular nucleophilic additions of a hydroxymethyl unit to ketones in β-hydroxyketones have been developed. The product obtained by this protocol was successfully converted to chiral A-ring moieties of Taxol™. Also developed was a promising silicon-tethered intramolecular α-alkylation reaction of the cyclic hydroxyketone.

KW - Alkylation

KW - Carbanion

KW - Intramolecular reaction

KW - Nucleophilic addition

KW - Silicon tethered

KW - Taxol™

UR - http://www.scopus.com/inward/record.url?scp=7044222313&partnerID=8YFLogxK

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DO - 10.1016/j.tetlet.2004.09.143

M3 - Article

AN - SCOPUS:7044222313

SN - 0040-4039

VL - 45

SP - 8647

EP - 8651

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

ER -

Development of silicon-tethered anionic reaction and its application to the synthesis of chiral A-ring moieties of Taxol™

Abstract

Keywords

ASJC Scopus subject areas

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