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A 15-step chemoenzymatic total synthesis of C-1 methoxycarbonyl narciclasine (<b>10</b>) was accomplished. The synthesis began with the toluene dioxygenase-mediated dihydroxylation of <i>ortho</i>-dibromobenzene to provide the corresponding <i>cis</i>-dihydrodiol (<b>12</b>) as a single enantiomer. Further key steps included a nitroso Diels–Alder reaction and an intramolecular Heck cyclization. The C-1 homolog <b>10</b> was tested and evaluated for antiproliferative activity against natural narciclasine (<b>1</b>) as the positive control. Experimental and spectral data are reported for all novel compounds.