Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 27th March 2019 from 11:00 AM to 1:00 PM (GMT).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 21, 2010
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 22 May 2010, accepted on 14 Jul 2010 and first published on 31 Aug 2010


Article type: Paper
DOI: 10.1039/C0OB00161A
Citation: Org. Biomol. Chem., 2010,8, 4940-4948

  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements