The naturally occurring cytotoxic cyclic guanidine isoptilocaulin has been shown to have medicinal properties making it a formidable antibiotic against both gram negative and gram positive bacteria, and the molecule has also been proven to be an effective chemotherapeutic agent, specifically against L1210 murine leukemia cells in vitro. To efficiently synthesize this molecule, we propose implementing a series of convergent reactions using an intramolecular Diels-Alder reaction to create the desired product, isoptilocaulin.

Efficient synthetic route to isopitlocaulin utilizing an intramolecular Diels-Alder reaction

245th National Meeting (2013)

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