Base-catalyzed oxidative dearomatization of multisubstituted phloroglucinols: An easy access to C-glucosyl 3, 5, 6-trihydroxycyclohexa-2, 4-dienone derivatives. (1st October 2019)

• Record Type: Journal Article
• Authors: Gao, Wan; Chen, Zhong; Yang, Yanan; Jiang, Jianshuang; Feng, Ziming; Zhang, Xu; Yuan, Xiang; Zhang, Peicheng
• Is Part Of: Carbohydrate research. Volume 484(2019)
• Publication Date: 2019-10-01
• Subjects: 3, 5, 6-Trihydroxycyclohexa-2, 4-dienone -- Oxidative dearomatization -- Quinochalcone C-Glucosides; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2019.107756
• Languages: English
• ISSNs: 0008-6215

Abstract

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. Graphical abstract: Image 1 Highlights: An efficient and simple method for the synthesis of C -glucosyl 3, 5, 6-trihydroxycyclohexa-2, 4-dienones was developed. The absolute configuration was determined by electronic circular dichroism (ECD) spectra. A plausible mechanism involving a singlet oxygen intermediate and a radical process is proposed.