Novel Method for Preparation of Monoesters of Symmetric Diphenolic Compounds like Curcumin (1,7‐Bis(4‐hydroxy‐3‐methoxy phenyl)‐1,6‐heptadiene‐3,5‐dione) via Solid‐Phase Synthesis

Abstract

Synthesis of a monoester of symmetrical diphenolic compound curcumin (1,7‐bis(4‐hydroxy‐3‐methoxy phenyl)‐1,6‐heptadiene‐3,5‐dione) with glycine has been carried out by anchoring one of its free phenolic groups to an insoluble polymeric solid‐support resin controlled pore glass‐long chain alkylamine (CPG‐LCAA) via a 2‐carbon linker by solid‐phase synthesis. The other free phenolic was esterified selectively with N‐protected glycinoyl chloride to give the monoester exclusively. Subsequent deprotection of the amino group and deblocking of the monoester from polymer support by treatment with hydriodic acid (HI) gave the desired product. We earlier reported synthesis of a large number of diesters of curcumin, but selective esterification of one phenolic has been accomplished by this novel method, which can be used for preparing monoesters of any symmetric diphenol in quantitative yields.

Keywords:

• CPG‐LCAA
• curcumin
• monoglycinoyl curcumin
• solid phase

Acknowledgment

One of the authors (S. K. D.) wish to thank University Grants Commission (UGC), India, for providing financial assistance in the form of a scholarship during the course of this study.