Osmium Tetroxide Oxidation of Hopa-15, 17(21)-diene, Dehydrozeorinin, and Hop-17(21)-ene

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Abstract

The structures of the diol and the conjugated ketone obtained from the osmium tetroxide oxidation of hopa-15, 17(21)-dienes (I) were now revised and correctly assigned as IV and V, respectively, the former being obtained by lithium aluminum hydride decomposition and the latter by hydrogen sulfide decomposition of the intermediate osmate. Hop-17(21)-ene (VI) was also found to give the seco-diketone (VIII) in lesser yield. A probable mechanism for the formation of the seco-diketones was also discussed.

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