Azomethine Ylide Cycloaddition Approach toward Dendrobine: Synthesis of 5-Deoxymubironine C

The Journal of Organic Chemistry
Benjamin M Williams, Dirk Trauner

Abstract

A concise route to the azatricyclo[6.2.1.04,11]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.

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Citations

Jul 30, 2019·Beilstein Journal of Organic Chemistry·Anthony ChoiIain Coldham
Aug 12, 2021·The Journal of Organic Chemistry·Martin J NealThomas D Montgomery
Jun 13, 2019·Organic Letters·Jingming CaoChi-Sing Lee

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