Concise synthesis of 3-C-glycosyl isocoumarins and 2-glycosyl-4H-chromen-4-ones.
Chem Commun (Camb)
; 60(75): 10390-10393, 2024 Sep 16.
Article
in En
| MEDLINE
| ID: mdl-39224044
ABSTRACT
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.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Chem Commun (Camb)
Year:
2024
Document type:
Article