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Williams, Benjamin M.; Trauner, Dirk (2018): Azomethine Ylide Cycloaddition Approach toward Dendrobine: Synthesis of 5-Deoxymubironine C. In: Journal of Organic Chemistry, Vol. 83, No. 6: pp. 3061-3068
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Abstract

A concise route to the azatricyclo[6.2.1.0(4,11)]undecane core of (-)-dendrobine and (-)-mubironine C is described wherein an unstabilized azomethine ylide cycloaddition provides the complete carbon framework of the natural products. The cyclization precursor is made in short order from (R)-carvone through an unconventional high-pressure Ireland Claisen reaction. Attempts to install a final hydroxyl group through an intramolecular lactonization strategy and the observation of an unexpected and highly complex enal-ene product are also reported.