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Issue 21, 2010
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Highly efficient macrolactonization of ω-hydroxy acids using benzotriazole esters: synthesis of Sansalvamide A

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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), 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.

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

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Supplementary files

Article information


Submitted
22 May 2010
Accepted
14 Jul 2010
First published
31 Aug 2010

Org. Biomol. Chem., 2010,8, 4940-4948
Article type
Paper

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

J. A. Morales-Serna, E. Sánchez, R. Velázquez, J. Bernal, E. García-Ríos, R. Gaviño, G. Negrón-Silva and J. Cárdenas, Org. Biomol. Chem., 2010, 8, 4940
DOI: 10.1039/C0OB00161A

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