Synthesis of naturally occurring naphthoquinone epoxides and application in the synthesis of beta-lapachone.
Optimized epoxidation conditions of mono- and dialkylated naphthoquinones are presented. Based on the epoxidation protocol making use of H(2)O(2)/Na(2)CO(3), naphthoquinone epoxides are obtained in high yields. The optimized epoxidation conditions are applied in a short and high yielding synthesis of the pharmaceutically important beta-lapachone.
Claessens
Sven
S
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000, Ghent, Belgium.
Habonimana
Pascal
P
De Kimpe
Norbert
N
D004852:Epoxy Compounds / Q000138:chemical synthesis*; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry*
D004852:Epoxy Compounds; D009285:Naphthoquinones; C014638:beta-lapachone