lycopodium “creeping cedar” › sites › chemistry.drupal.ku.edu › ...t-buli _78 0 c; i-amono...
TRANSCRIPT
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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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JACS 2013, ASAP; JACS 2011, 418
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Mechanism? Class (name) of rxn
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Hendrick J. Prins
A unique gold-catalyzed alkynyl Prins
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Ring expansion
Danheiser TL 1981 4205
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Formation of 10: conrotatory or disrotatory…what would Fukui say?
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Mechanism? Regiochemistry? Explain disrotatory ring opening.
Buchner ring expansion (a modern take – Synlett 2011, 1449)
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Reagents??
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Ac2O, CSA, tol, reflux
Mechanism?, Name?
Mechanism?
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Mechanism?