Divergent Cascade Construction of Skeletally Diverse “Privileged” Pyrazole-Derived Molecular Architectures

Yongqiang Zhang; Shanchao Wu; Shengzheng Wang; Kun Fang; Guoqiang Dong; Na Liu; Zhenyuan Miao; Jianzhong Yao; Jian Li; Wannian Zhang; Chunquan Sheng; Wei Wang

doi:10.1002/ejoc.201403673

Divergent Cascade Construction of Skeletally Diverse “Privileged” Pyrazole-Derived Molecular Architectures

Yongqiang Zhang, Shanchao Wu, Shengzheng Wang, Kun Fang, Guoqiang Dong, Na Liu, Zhenyuan Miao, Jianzhong Yao, Jian Li, Wannian Zhang, Chunquan Sheng, Wei Wang

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

54 Scopus citations

Abstract

A powerful divergent cascade strategy has been explored for the easy construction of diverse enantioenriched pyrazole-derived scaffolds from readily available chiral fused pyrazole-tetrahydropyran acetals. These versatile intermediates can react in various ways to give Michael–aldol, reduction–lactonization, α-hydroxylation–acetalization–oxidation, and Wittig–aldol and Wittig–oxa-Michael cascade reactions. Using only six simple building blocks, these processes gave five distinct molecular architectures. Furthermore, screening 10 compounds representing the 5 distinct scaffolds revealed potent anticancer lead compounds that deserve further development.

Original language	English (US)
Pages (from-to)	2030-2037
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	9
DOIs	https://doi.org/10.1002/ejoc.201403673
State	Published - Mar 2015
Externally published	Yes

Keywords

Divergent synthesis
Drug design
Molecular diversity
Nitrogen heterocycles
Organocatalysis
Spiro compounds

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201403673

Cite this

Divergent Cascade Construction of Skeletally Diverse “Privileged” Pyrazole-Derived Molecular Architectures. / Zhang, Yongqiang; Wu, Shanchao; Wang, Shengzheng; Fang, Kun; Dong, Guoqiang; Liu, Na; Miao, Zhenyuan; Yao, Jianzhong; Li, Jian; Zhang, Wannian; Sheng, Chunquan; Wang, Wei.

In: European Journal of Organic Chemistry, Vol. 2015, No. 9, 03.2015, p. 2030-2037.

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

Zhang, Yongqiang ; Wu, Shanchao ; Wang, Shengzheng ; Fang, Kun ; Dong, Guoqiang ; Liu, Na ; Miao, Zhenyuan ; Yao, Jianzhong ; Li, Jian ; Zhang, Wannian ; Sheng, Chunquan ; Wang, Wei. / Divergent Cascade Construction of Skeletally Diverse “Privileged” Pyrazole-Derived Molecular Architectures. In: European Journal of Organic Chemistry. 2015 ; Vol. 2015, No. 9. pp. 2030-2037.

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abstract = "A powerful divergent cascade strategy has been explored for the easy construction of diverse enantioenriched pyrazole-derived scaffolds from readily available chiral fused pyrazole-tetrahydropyran acetals. These versatile intermediates can react in various ways to give Michael–aldol, reduction–lactonization, α-hydroxylation–acetalization–oxidation, and Wittig–aldol and Wittig–oxa-Michael cascade reactions. Using only six simple building blocks, these processes gave five distinct molecular architectures. Furthermore, screening 10 compounds representing the 5 distinct scaffolds revealed potent anticancer lead compounds that deserve further development.",

keywords = "Divergent synthesis, Drug design, Molecular diversity, Nitrogen heterocycles, Organocatalysis, Spiro compounds",

author = "Yongqiang Zhang and Shanchao Wu and Shengzheng Wang and Kun Fang and Guoqiang Dong and Na Liu and Zhenyuan Miao and Jianzhong Yao and Jian Li and Wannian Zhang and Chunquan Sheng and Wei Wang",

note = "Funding Information: The authors thank the National Natural Science Foundation of China (NSFC) (grant 81222044 to C. S. and 21372073 to W. W.), the 863 Hi-Tech Program of China (grant 2014AA020525 to C. S.), and the National Basic Research Program of China (grant 2014CB541800 to C. S.). Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/ejoc.201403673",

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AU - Fang, Kun

AU - Dong, Guoqiang

AU - Liu, Na

AU - Miao, Zhenyuan

AU - Yao, Jianzhong

AU - Li, Jian

AU - Zhang, Wannian

AU - Sheng, Chunquan

AU - Wang, Wei

N1 - Funding Information: The authors thank the National Natural Science Foundation of China (NSFC) (grant 81222044 to C. S. and 21372073 to W. W.), the 863 Hi-Tech Program of China (grant 2014AA020525 to C. S.), and the National Basic Research Program of China (grant 2014CB541800 to C. S.). Publisher Copyright: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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N2 - A powerful divergent cascade strategy has been explored for the easy construction of diverse enantioenriched pyrazole-derived scaffolds from readily available chiral fused pyrazole-tetrahydropyran acetals. These versatile intermediates can react in various ways to give Michael–aldol, reduction–lactonization, α-hydroxylation–acetalization–oxidation, and Wittig–aldol and Wittig–oxa-Michael cascade reactions. Using only six simple building blocks, these processes gave five distinct molecular architectures. Furthermore, screening 10 compounds representing the 5 distinct scaffolds revealed potent anticancer lead compounds that deserve further development.

AB - A powerful divergent cascade strategy has been explored for the easy construction of diverse enantioenriched pyrazole-derived scaffolds from readily available chiral fused pyrazole-tetrahydropyran acetals. These versatile intermediates can react in various ways to give Michael–aldol, reduction–lactonization, α-hydroxylation–acetalization–oxidation, and Wittig–aldol and Wittig–oxa-Michael cascade reactions. Using only six simple building blocks, these processes gave five distinct molecular architectures. Furthermore, screening 10 compounds representing the 5 distinct scaffolds revealed potent anticancer lead compounds that deserve further development.

KW - Divergent synthesis

KW - Drug design

KW - Molecular diversity

KW - Nitrogen heterocycles

KW - Organocatalysis

KW - Spiro compounds

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Divergent Cascade Construction of Skeletally Diverse “Privileged” Pyrazole-Derived Molecular Architectures

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Keywords

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