Expedient Construction of the [7–5–5] All-Carbon Tricyclic Core of the Daphniphyllum Alkaloids Daphnilongeranin B and Daphniyunnine D
2012; American Chemical Society; Volume: 14; Issue: 7 Linguagem: Inglês
10.1021/ol3002267
ISSN1523-7060
AutoresBenjamin Darses, Iacovos N. Michaelides, Filippo Sladojevich, John W. Ward, P. Rzepa, Darren J. Dixon,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoA synthetic strategy for the construction of the [7-5-5] all-carbon tricyclic core of numerous calyciphylline A-type Daphniphyllum alkaloids has been developed using a key intramolecular Pauson-Khand reaction. A subsequent base-mediated double-bond migration and a regio- and stereoselective radical late stage allylic oxygenation provide access to the substitution patterns of daphnilongeranin B and daphniyunnine D.
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