Oxone®-Mediated Direct α-Hydroxylation of β-Dicarbonyl Compounds: Racemic Synthesis of Harzialactone A

• Main Author: Sá,Marcus M.
• Publication Date: 2019
• Other Authors: Peterle,Marcos M., Marques,Marcelo V.
• Format: Article
• Language: eng
• Source: Journal of the Brazilian Chemical Society (Online)
• Download full: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000801779
• topic: harzialactone; α-hydroxylation; α-hydroxy malonates; α-hydroxy-γ-lactone; Oxone®

An environmentally benign method is described for the α-hydroxylation of malonates and cyclic analogues in aqueous medium at room temperature under mild conditions, based on the in situ generation of dimethyldioxirane through the combination of acetone and Oxone®. This procedure was found to be substrate-dependent and was successfully performed to provide α-hydroxylated γ-lactones. To demonstrate the synthetic potential of this mild α-hydroxylation, two different concise routes were developed to synthesize harzialactone A in the racemic form with a moderate (3:1) diastereomeric ratio.