Synthesis and reactivity of 1,2-dioxolanes from β,γ-epoxy ketones.
Five-membered ring peroxides were prepared in one step in 31-86% yield from readily accessible β,γ-epoxy ketones and H2O2. The reaction proceeded via a tetrahydrofuran, which was converted to the thermodynamically favored 1,2-dioxolane. The product contains a leaving group, which can be displaced to synthesize analogues of the plakinic acid natural products.
Department of Chemistry, New York University , 100 Washington Square East, New York, New York 10003, United States.
Wynne V
WV
Kandur
Kathleen J
KJ
Richert
Curtis J
CJ
Rieder
Andrew M
AM
Thomas
Chunhua
C
Hu
Joseph W
JW
Ziller
K A
KA
Woerpel
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D004148:Dioxolanes / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010545:Peroxides / Q000737:chemistry*
D001688:Biological Products; D004148:Dioxolanes; D004852:Epoxy Compounds; D007659:Ketones; D010545:Peroxides; C516353:plakinic acid A