4 years ago

One-Step Multigram-Scale Biomimetic Synthesis of Psiguadial B

One-Step Multigram-Scale Biomimetic Synthesis of Psiguadial B
Matthew D. Wodrich, Duc N. Tran, Nicolai Cramer, Christopher G. Newton
A 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. A one-step multigram-scale synthesis of psiguadial B has been achieved using a biomimetic three-component coupling, thus generating three C−C bonds, one C−O bond, two rings, and four stereocenters. Combined synthetic and computational experiments suggest the reaction proceeds by a Michael addition of caryophyllene to an in situ generated ortho-quinone methide, followed by two sequential cationic cyclization events.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201708333

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