Newton, Christopher G.Tran, Duc N.Wodrich, Matthew D.Cramer, Nicolai2017-12-042017-12-042017-12-04201710.1002/anie.201708333https://infoscience.epfl.ch/handle/20.500.14299/142626WOS:000413314800042A gram-scale synthesis of psiguadial B, a purported inhibitor of human hepatoma cell growth, has been achieved in one step by a biomimetic three-component coupling of caryophyllene, benzaldehyde, and diformylphloroglucinol. This cascade reaction is catalyzed by N, N'-dimethylethylenediamine, and proceeds at ambient temperature to generate four stereocenters, two rings, one C-O bond, and three C-C bonds. Combined computational and experimental investigations suggest the biosynthesis of the natural product is non-enzyme mediated, and is the result of a Michael addition between caryophyllene and a reactive ortho-quinone methide, followed by two sequential intramolecular cationic cyclization events.biomimetic synthesiscyclizationnatural productsterpenoidstotal synthesistext::journal::journal article::research article