Azomethine Ylide Cycloaddition Approach toward Dendrobine: Synthesis of 5-Deoxymubironine C.
- Resource Type
- Article
- Authors
- Williams, Benjamin M.; Trauner, Dirk
- Source
- Journal of Organic Chemistry. 3/16/2018, Vol. 83 Issue 6, p3061-3068. 8p.
- Subject
- Language
- ISSN
- 0022-3263
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. [ABSTRACT FROM AUTHOR]