Synthesis of antifungal alatanone and trineurone polyketides

Synthesis of antifungal alatanone and trineurone polyketides

[Display omitted] The antifungal polyketides alatanones A and B and trineurones A–E have been synthesized using a one-pot C-acylation reaction coupling 1,3-cyclohexanediones with the appropriate carboxylic acids. This key transformation is believed to proceed via initial carbodiimide-mediated O-acyl...

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Veröffentlicht in:Tetrahedron letters 2016-03, Vol.57 (10), p.1083-1086
Hauptverfasser: Lewis, Alexander R., Reber, Keith P.
Format: Artikel
Sprache:eng
Schlagworte:
Antifungal activity
Carboxylic acids
Coupling
Enolate C-acylation
Migration
Natural products
Polyketide
Synthesis
Tetrahedrons
Total synthesis
Transformations
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Zusammenfassung:[Display omitted] The antifungal polyketides alatanones A and B and trineurones A–E have been synthesized using a one-pot C-acylation reaction coupling 1,3-cyclohexanediones with the appropriate carboxylic acids. This key transformation is believed to proceed via initial carbodiimide-mediated O-acylation followed by a DMAP-catalyzed Claisen–Haase rearrangement, resulting in O to C acyl migration.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.01.090