Organic letters

Efficient construction of the oxatricyclo [6.3. 1.00, 0] dodecane core of komaroviquinone using a cyclization/cycloaddition cascade of a rhodium carbenoid intermediate

A Padwa, J Boonsombat, P Rashatasakhon…

Index: Padwa, Albert; Boonsombat, Jutatip; Rashatasakhon, Paitoon; Willis, Jerremey Organic Letters, 2005 , vol. 7, # 17 p. 3725 - 3727

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Citation Number: 43

Abstract

The rhodium (II)-catalyzed cyclization/cycloaddition cascade of ao-carbomethoxyaryl diazo dione is described as a potential route to the oxatricyclo [6.3. 1.00, 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.