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Lycopodium “creeping cedar” › sites › chemistry.drupal.ku.edu › ...t-BuLi _78 0 C; i-AmONO...

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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

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