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

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 y...

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Published inChemical 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
LanguageEnglish
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
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Summary: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.
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d4cc03004d