Concise synthesis of 3-C-glycosyl isocoumarins and 2-glycosyl-4H-chromen-4-ones

• Published in: Chemical communications (Cambridge, England) Vol. 60; no. 75; pp. 10390 - 10393
• Main Authors: Liu, Deng-Yin, Ruan, Yu-Jun, Wang, Xiao-Li, Hu, Xin-Yue, Wang, Peng-Fei, Wen, Miao-Miao, Zhang, Cong-Zhen, Xiao, Yu-He, Liu, Xu-Ge
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 16.09.2024; Royal Society of Chemistry
• Subjects: Benzoic acid; Carbonyls; Chemical synthesis; Chemistry; Chemistry, Multidisciplinary; Glycogens; Glycosides; Hydroxybenzaldehydes; Natural products; Physical Sciences; Science & Technology; Stereoselectivity; Substrates
• ISSN: 1359-7345; 1364-548X; 1364-548X
• DOI: 10.1039/d4cc03004d

A new Ru-catalyzed C-H activation/cyclization reaction for the synthesis of 3-C-glycosyl isocoumarins and 2-glycosyl-4H-chromen-4-ones with carbonyl sulfoxonium ylide glycogen are reported. In this catalytic system, benzoic acid and its derivatives react with carbonyl sulfoxonium ylide glycogen to yield isocoumarin C-glycosides, while 2-hydroxybenzaldehyde substrates react to produce chromone C-glycosides. These reactions were characterized by mild reaction conditions, broad substrate scope, high functional-group compatibility, and high stereoselectivity to yield several high-value isocoumarins and chromone skeleton-containing C-glycosides. The methods were successfully implemented in the context of large-scale reactions and the late-stage modification of complex natural products.