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The naturally occurring but scarce marine neurotoxins azaspiracids-1, -2, and -3 have been synthesized from five key building blocks by a convergent strategy that involved dithiane and Stille coupling reactions. The ABCD fragments were constructed through a cascade reaction involving deprotection/self-assembly of the precursors, while the FGHI fragment was(More)
As the largest secondary metabolite to be discovered as of yet, the polyether marine neurotoxin maitotoxin constitutes a major structural and synthetic challenge. After its originally proposed structure ( 1) had been questioned on the basis of biosynthetic considerations, we provided computational and experimental support for structure 1. In an effort to(More)
We report a detailed investigation into the application of visible light-mediated photocatalysis to a challenging bond construction in a complex pharmaceutical target. The optimized reaction allowed the direct coupling of N-methylmorpholine with an unfunctionalized pyridazine in good yield and selectivity, and with high purity of the product isolated via(More)
The ABD-ring of phomactin A was synthesized using an intramolecular formal oxa-[3 + 3] cycloaddion of an alpha,beta-unsaturated iminium salt tethered to a 1,3-diketone. This represents the first time that the 12-membered ring has been formed simultaneously with the 1-oxadecalin and should afford a facile route to the challenging structure of phomactin A.(More)
A visible-light-mediated radical Smiles rearrangement has been developed to address the challenging synthesis of the gem-difluoro group present in an opioid receptor-like 1 (ORL-1) antagonist that is currently in development for the treatment of depression and/or obesity. This method enables the direct and efficient introduction of the difluoroethanol motif(More)
The large number of reagents that have been developed for the synthesis of trifluoromethylated compounds is a testament to the importance of the CF3 group as well as the associated synthetic challenge. Current state-of-the-art reagents for appending the CF3 functionality directly are highly effective; however, their use on preparative scale has minimal(More)
The title (1H-pyrrol-2-yl)pyridines, C(9)H(8)N(2), substituted at the ortho, meta, and para positions of the pyridine ring all have hydrogen-bonded arrangements with geometrically similar, nearly linear, N(pyrrole)-H...N(pyridine) hydrogen bonds of average length. The graph sets for the ortho, meta, and three para polymorphs are R(2)(2)(10), C(6), C(7),(More)