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Efficient Construction of the Oxatricyclo[,0]dodecane Core of Komaroviquinone Using a Cyclization/Cycloaddition Cascade of a Rhodium Carbenoid Intermediate

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journal contribution
posted on 18.08.2005, 00:00 by Albert Padwa, Jutatip Boonsombat, Paitoon Rashatasakhon, Jerremey Willis
The rhodium(II)-catalyzed cyclization/cycloaddition cascade of a o-carbomethoxyaryl diazo dione is described as a potential route to the oxatricyclo[,0]dodecane substructure of the icetexane diterpene komaroviquinone. The initially formed carbonyl ylide dipole prefers to cyclize to an epoxide at 25 °C but can be induced to undergo cycloaddition across the tethered π-bond at higher temperatures.