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Isolation: J. Org. Chem. 2001, 5901; Bioorg. Med. Chem. 2006, 5995. lyconadin A is weakly cytotoxic (IC50 0.46 mg/mL against murine lymphoma) lyconadin B is not cytotoxic Lycopodium “creeping cedar”

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  • Isolation: J. Org. Chem. 2001, 5901; Bioorg. Med. Chem. 2006, 5995. lyconadin A is weakly cytotoxic (IC50 0.46 mg/mL against murine lymphoma) lyconadin B is not cytotoxic

    Lycopodium “creeping cedar”

  • JACS 2013, ASAP; JACS 2011, 418

  • Mechanism? Class (name) of rxn

  • Hendrick J. Prins

    A unique gold-catalyzed alkynyl Prins

  • Ring expansion

    Danheiser TL 1981 4205

  • Formation of 10: conrotatory or disrotatory…what would Fukui say?

  • Mechanism? Regiochemistry? Explain disrotatory ring opening.

    Buchner ring expansion (a modern take – Synlett 2011, 1449)

  • Reagents??

  • Ac2O, CSA, tol, reflux

    Mechanism?, Name?

    Mechanism?

  • Mechanism?