Journal of Organic Chemistry 2013-06-21

A model system for the synthesis of complanadine alkaloids by "diverted Kondrat'eva" oxazole-olefin cycloaddition.

Mario Uosis-Martin, G Dan Pantoş, Mary F Mahon, Simon E Lewis

Index: J. Org. Chem. 78(12) , 6253-63, (2013)

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Abstract

A synthetic approach to complanadine alkaloids is described which employs a Kondrat'eva reaction to construct the pyridine rings. The viability of this approach is demonstrated by its application to a model substrate accessed from unfunctionalized decalin. The key transformation affords the desired tetracyclic architecture with unprecedented incorporation of substituents on the pyridine ring, implicating the oxazole α-hydroxy group as an active participant in the cycloadduct fragmentation process.