Total synthesis and glycosidase inhibition of broussonetine i and J 2

Hui Zhao; Atsushi Kato; Kasumi Sato; Yue Mei Jia; Chu Yi Yu

doi:10.1021/jo4010553

Total synthesis and glycosidase inhibition of broussonetine i and J ₂

Hui Zhao, Atsushi Kato, Kasumi Sato, Yue Mei Jia, Chu Yi Yu^*

^*Corresponding author for this work

Hospital Pharmacy

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

37 Scopus citations

Abstract

The first total synthesis of both broussonetine I and J₂ together with their enantiomers have been accomplished via the same synthetic route through 18 and 16 steps in excellent overall yields (18% and 19%, respectively), starting from R-glyceraldehyde. Broussonetine I was found to be a potent inhibitor of β-glucosidase (IC₅₀ = 2.9 μM), while ent-broussonetine I and ent-broussonetine J₂ were found to be potent inhibitors of α-glucosidase (IC₅₀ = 0.33 and 0.53 μM, respectively).

Original language	English
Pages (from-to)	7896-7902
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	78
Issue number	16
DOIs	https://doi.org/10.1021/jo4010553
State	Published - 2013/08/16

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo4010553

Cite this

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title = "Total synthesis and glycosidase inhibition of broussonetine i and J 2",

abstract = "The first total synthesis of both broussonetine I and J2 together with their enantiomers have been accomplished via the same synthetic route through 18 and 16 steps in excellent overall yields (18% and 19%, respectively), starting from R-glyceraldehyde. Broussonetine I was found to be a potent inhibitor of β-glucosidase (IC50 = 2.9 μM), while ent-broussonetine I and ent-broussonetine J2 were found to be potent inhibitors of α-glucosidase (IC50 = 0.33 and 0.53 μM, respectively).",

author = "Hui Zhao and Atsushi Kato and Kasumi Sato and Jia, {Yue Mei} and Yu, {Chu Yi}",

year = "2013",

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journal = "Journal of Organic Chemistry",

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T1 - Total synthesis and glycosidase inhibition of broussonetine i and J 2

AU - Zhao, Hui

AU - Kato, Atsushi

AU - Sato, Kasumi

AU - Jia, Yue Mei

AU - Yu, Chu Yi

PY - 2013/8/16

Y1 - 2013/8/16

N2 - The first total synthesis of both broussonetine I and J2 together with their enantiomers have been accomplished via the same synthetic route through 18 and 16 steps in excellent overall yields (18% and 19%, respectively), starting from R-glyceraldehyde. Broussonetine I was found to be a potent inhibitor of β-glucosidase (IC50 = 2.9 μM), while ent-broussonetine I and ent-broussonetine J2 were found to be potent inhibitors of α-glucosidase (IC50 = 0.33 and 0.53 μM, respectively).

AB - The first total synthesis of both broussonetine I and J2 together with their enantiomers have been accomplished via the same synthetic route through 18 and 16 steps in excellent overall yields (18% and 19%, respectively), starting from R-glyceraldehyde. Broussonetine I was found to be a potent inhibitor of β-glucosidase (IC50 = 2.9 μM), while ent-broussonetine I and ent-broussonetine J2 were found to be potent inhibitors of α-glucosidase (IC50 = 0.33 and 0.53 μM, respectively).

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DO - 10.1021/jo4010553

M3 - 学術論文

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AN - SCOPUS:84882389080

SN - 0022-3263

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EP - 7902

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 16