A number of our current studies are driven by a hypothesis that the biosynthesis of the natural product in question involves a key step that is non-enzyme-mediated (i.e., spontaneous). I will present findings in the context of ottelione A (1 ), paracaseolide A (2 ), and the hydrocarbon core 3  of the 9-membered enediyne family of natural products. Finally, I will recount how this last set of studies took an unexpected turn (i.e., serendipitous) that revealed the hexadehydro-Diels�Alder (HDDA) reaction (e.g., cf. 4  to 5 ).1 1 Hoye, T. R.; Baire, B.; Niu, D.; Willoughby, P. H.; Woods, B. P. The hexadehydro-Diels�Alder reaction. Nature 2012  , 490, 208�212.

Natural product explorations: From spontaneity to serendipity

245th National Meeting (2013)

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