The first total synthesis of resorcyclic acid lactone spiroketal citreoviranol (1) is described. The synthesis was completed in nine steps and via Sonogashira cross-coupling, gold-catalyzed cyclization, and an unusual base-induced ketalization. The relative and absolute stereochemistry of citreoviranol was unambiguously confirmed using 2D NMR spectroscopy and X-ray crystallography.
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| http://dx.doi.org/10.1021/acs.joc.6b01503 | DOI Listing |
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