Base-catalyzed oxidative dearomatization of multisubstituted phloroglucinols: An easy access to C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives

Wan Gao; Zhong Chen; Yanan Yang; Jianshuang Jiang; Ziming Feng; Xu Zhang; Xiang Yuan; Peicheng Zhang

doi:10.1016/j.carres.2019.107756

Base-catalyzed oxidative dearomatization of multisubstituted phloroglucinols: An easy access to C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives

Carbohydr Res. 2019 Oct 1:484:107756. doi: 10.1016/j.carres.2019.107756. Epub 2019 Aug 5.

Authors

Wan Gao¹, Zhong Chen¹, Yanan Yang¹, Jianshuang Jiang¹, Ziming Feng¹, Xu Zhang¹, Xiang Yuan¹, Peicheng Zhang²

Affiliations

¹ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, China.
² State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, China. Electronic address: pczhang@imm.ac.cn.

PMID: 31421352
DOI: 10.1016/j.carres.2019.107756

Abstract

An efficient and simple method for the protecting group-free synthesis of C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone has been firstly established. This method is compatible with various functional groups, such as benzyl and phenethyl groups, affording a range of C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives.

Keywords: 3,5,6-Trihydroxycyclohexa-2,4-dienone; Oxidative dearomatization; Quinochalcone C-Glucosides.

MeSH terms

Carbohydrate Conformation
Carbohydrate Sequence
Catalysis
Glucosides / chemical synthesis*
Glucosides / chemistry
Oxidation-Reduction
Phloroglucinol / chemistry*
Stereoisomerism

Substances

Glucosides
Phloroglucinol