Journal of Organic Chemistry p. 2593 - 2597 (1988)
Update date:2022-08-03
Topics:
Govindan, S. V.
Fuchs, P. L.
A two-step method for oxidation of olefins to α-diketones is presented.Tricyclic olefin 12 was converted to three stereodefined 1,2-diols 14, 15, and 16.Swern oxidation of each of these substrates gave the same enolized α-diketone 17; base-catalyzed isomerization of this material quantitatively afforded an isomerized α-diketone 7B bearing the substitution pattern found in the antileukemia agent bruceantin (1A).The four α-diketones prepared are reasonably cytotoxic against P388 mouse leukemia.
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(1987)
