Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Total Synthesis of (−)-Xylogranatopyridine B via a Palladium-Catalyzed Oxidative Stannylation of Enones

Total Synthesis of (−)-Xylogranatopyridine B via a Palladium-Catalyzed Oxidative Stannylation of Enones
Alexander W. Schuppe, Yifeng Chen, David Huang, Timothy R. Newhouse
We report a total synthesis of the pyridine-containing limonoid alkaloid (−)-xylogranatopyridine B in 11 steps from commercially available dihydrocarvone. The central pyridine ring was assembled by a late-stage fragment coupling approach employing a modified Liebeskind pyridine synthesis. One fragment was prepared by an allyl-palladium catalyzed oxidative enone β-stannylation, in which the key bimetallic β-stannyl palladium enolate intermediate undergoes a β-hydride elimination. This methodology also allowed introduction of alkyl and silyl groups to the β-position of enones.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b13189

DOI: 10.1021/jacs.7b13189

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