Yamaguchi Esterification:

What is Yamaguchi macrolactonization?

The development of high number ring lactones from hydroxy acids employing Yamaguchi reagent (2,4,6-trichlorobenzoyl chloride/DMAP) is known as the Yamaguchi macrolactonization

Yamaguchi Esterification

The best solvent forms this transformation is aliphatic hydrocarbon; Yamaguchi macrolactonization is used to prepare lactones and esters of the corresponding mixed anhydrides. The starting material acid was reacted with 2,4,6-trichlorobenzoyl chloride in the presence of NEt3, by removing triethylamine hydrochloride.

The formed mixed anhydride after refluxing with DMAP The desired product macrolactone will form. To avoid intramolecular coupling, product dilute is more with respective solvent. DMAP reagent mechanism and Yamaguchi mechanism are shown below

Yamaguchi Macrolactonization Mechanism

Yamaguchi Macrolactonization Mechanism

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