Synthesis of antifungal alatanone and trineurone polyketides

• DOI: 10.1016/j.tetlet.2016.01.090
• Publication Date: 2016-01-27T22:25:11Z
• Authors: Alexander R. Lewis; Keith P. Reber
• Keywords: Carbodiimide

Abstract 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.