Humulones and lupulones have affirmed themselves as key ingredients in the multi-billion dollar brewing industry. Originally exploited for their bacteriostatic properties, these compounds also exhibit high levels of biological activity against a variety of diseases. Our investigations are towards developing a synthetic route to a library of humulones, lupulones, and their derivatives as possible biologically active agents against myriad diseases. Prenylation of acylphloroglucinol (1) yields a mix of lupulones and bisprenylated acylphloroglucinols (2). The key step in our efficient syntheses of individual humulones (3) is a copper-mediated asymmetric oxidative dearomatization involving chiral sparteine ligands and an oxo-copper species developed by Porco, et al. Our investigations are also leading towards the diasteromeric adhumulones and determining the chirality of natural adhumulone. Active agents may lead to a transformation in hops as sources to the next generation of medicines.

Exploring hops chemistry: Towards efficient, asymmetric syntheses of humulones and lupulones

251st National Meeting (2016)

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