Synthesis of 7-substituted benzolactam-V8s and their selectivity for protein kinase C isozymes

Dawei Ma; Guozhi Tang; Alan P. Kozikowski

doi:10.1021/ol026125l

Synthesis of 7-substituted benzolactam-V8s and their selectivity for protein kinase C isozymes

Dawei Ma, Guozhi Tang, Alan P. Kozikowski

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

33 Scopus citations

Abstract

(Matrix Presented) Condensation of L-valine benzyl ester toluenesulfonic acid salt with a substituted cyclohexadione followed by aromatization with the assistance of NBS provides an N-aryl L-valine benzyl ester. This intermediate is converted into 7-substituted benzolactam-V8s using an asymmetric Strecker reaction as the key step. The target molecules show a different pattern of isozyme selectivity relative to the 8-substituted benzolactam-V8s.

Original language	English (US)
Pages (from-to)	2377-2380
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	14
DOIs	https://doi.org/10.1021/ol026125l
State	Published - Jul 11 2002
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol026125l

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abstract = "(Matrix Presented) Condensation of L-valine benzyl ester toluenesulfonic acid salt with a substituted cyclohexadione followed by aromatization with the assistance of NBS provides an N-aryl L-valine benzyl ester. This intermediate is converted into 7-substituted benzolactam-V8s using an asymmetric Strecker reaction as the key step. The target molecules show a different pattern of isozyme selectivity relative to the 8-substituted benzolactam-V8s.",

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AU - Ma, Dawei

AU - Tang, Guozhi

AU - Kozikowski, Alan P.

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Y1 - 2002/7/11

N2 - (Matrix Presented) Condensation of L-valine benzyl ester toluenesulfonic acid salt with a substituted cyclohexadione followed by aromatization with the assistance of NBS provides an N-aryl L-valine benzyl ester. This intermediate is converted into 7-substituted benzolactam-V8s using an asymmetric Strecker reaction as the key step. The target molecules show a different pattern of isozyme selectivity relative to the 8-substituted benzolactam-V8s.

AB - (Matrix Presented) Condensation of L-valine benzyl ester toluenesulfonic acid salt with a substituted cyclohexadione followed by aromatization with the assistance of NBS provides an N-aryl L-valine benzyl ester. This intermediate is converted into 7-substituted benzolactam-V8s using an asymmetric Strecker reaction as the key step. The target molecules show a different pattern of isozyme selectivity relative to the 8-substituted benzolactam-V8s.

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Synthesis of 7-substituted benzolactam-V8s and their selectivity for protein kinase C isozymes

Abstract

ASJC Scopus subject areas

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