871333-53-8Relevant academic research and scientific papers
Highly efficient macrolactonization of ω-hydroxy acids using benzotriazole esters: Synthesis of Sansalvamide A
Morales-Serna, Jose Antonio,Sanchez, Ericka,Velazquez, Ricardo,Bernal, Jorge,Garcia-Rios, Erendira,Gavino, Ruben,Negron-Silva, Guillermo,Cardenas, Jorge
experimental part, p. 4940 - 4948 (2010/11/24)
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), tetrabutylammonium tetrafluoroborate (TBABF4) and BF3·Et2O, respectively. A calcined hydrotalcite was also used instead of DMAP. Finally, to test the scope of the protocol in the synthesis of biologically relevant macrolactones, the total synthesis of Sansalvamide A was carried out.
