Facile synthesis of 4 ''-O-alkyl-(-)- EGCG derivatives through regioselective deacetylative alkylation

Abstract

Therapeutic potential of the D-ring methyl ethers of (-)-epigallocatechin-3- gallate [(-)- EGCG] warrants extensive structure-activity relationship study of various D-ring ethers of (-)-EGCG but, for this purpose, efficient synthetic strategy needs to be developed. In this study, efficient preparation of the 4 ''-O-alkyl-(-)-EGCGs (4a-e) was demonstrated using KI/K2CO3-promoted deacetylative alkylation of peracetyl (-)-EGCG, which could be broadly utilized for the preparation of various D-ring alkyl ethers of (-)-EGCG and thereby extensive structure-activity relationship study.