| Highly efficient macrolactonization of ω-hydroxy acids using benzotriazole esters: synthesis of Sansalvamide A. | |
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MedLine Citation:
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PMID: 20820651 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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 (TBABF(4)) and BF(3)·Et(2)O, 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. |
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Authors:
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José Antonio Morales-Serna; Ericka Sánchez; Ricardo Velázquez; Jorge Bernal; Eréndira García-Ríos; Rubén Gaviño; Guillermo Negrón-Silva; Jorge Cárdenas |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2010-08-31 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: 8 ISSN: 1477-0539 ISO Abbreviation: Org. Biomol. Chem. Publication Date: 2010 Nov |
Date Detail:
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Created Date: 2010-10-14 Completed Date: 2011-02-01 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: England |
Other Details:
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Languages: eng Pagination: 4940-8 Citation Subset: IM |
Affiliation:
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Instituto de Química, Universidad Nacional Autónoma de México Circuito Exterior, Ciudad Universitaria, Coyoacán 04510, México D.F., México. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Depsipeptides
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chemical synthesis*,
chemistry Esters / chemical synthesis, chemistry Hydroxy Acids / chemical synthesis, chemistry* Triazoles / chemical synthesis, chemistry* |
| Chemical | |
Reg. No./Substance:
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0/Depsipeptides; 0/Esters; 0/Hydroxy Acids; 0/Triazoles; 0/sansalvamide A; 27556-51-0/benzotriazole |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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