Synthesis of a 3,4,5-trimethoxybenzoyl ester analogue of epigallocatechin-3-gallate (EGCG): a potential route to the natural product green tea catechin, EGCG.
The synthesis of a trimethoxybenzoyl ester (D-ring) analogue of epigallocatechin-3-gallate (EGCG) is described. The versatile synthesis route can be used to synthesize A, B, and D ring analogues of EGCG and involves a key cyclization of the chalcone to the 3-flavene. This synthesis provides a possible route to the polyphenolic green tea natural product EGCG.
Zaveri
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Pharmaceutical Discovery Division, SRI International, 333 Ravenswood Avenue, Menlo Park, California 94025, USA. nurulain.zaveri@sri.com
D002392:Catechin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013662:Tea
D004952:Esters; D007202:Indicators and Reagents; D013662:Tea; D002392:Catechin; C045651:epigallocatechin gallate