Highly efficient macrolactonization of ω-hydroxy acids using benzotriazole esters: synthesis of Sansalvamide A

JA Morales-Serna, E Sánchez, R Velázquez…

Index: Morales-Serna, Jose Antonio; Sanchez, Ericka; Velazquez, Ricardo; Bernal, Jorge; Garcia-Rios, Erendira; Gavino, Ruben; Negron-Silva, Guillermo; Cardenas, Jorge Organic and Biomolecular Chemistry, 2010 , vol. 8, # 21 p. 4940 - 4948

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Citation Number: 13

Abstract

A facile and mild macrolactonization reaction of ω-hydroxy acids was developed based on the transesterification of benzotriazole esters. Treatment of ω-hydroxy acids with 1-ethyl-3-(3- dimethylaminopropyl) carbodiimide (EDC) and 1-hydroxy benzotriazole (HOBT) in chloroform provided macrolactones in excellent yields. The reactions were performed under basic, neutral and acidic conditions using N, N-dimethylaminopyridine (DMAP), ...