Total synthesis of (±)-nicolaioidesin B via a highly regio- and diastereoselective Diels–Alder reaction

Total synthesis of (±)-nicolaioidesin B via a highly regio- and diastereoselective Diels–Alder reaction

[Display omitted] The total synthesis of (±)-nicolaioidesin B, a natural product that shows preferential cytotoxicity against pancreatic cancer cells under nutrient starvation conditions, is achieved. The key step is a thermally-induced, highly regio- and diastereoselective Diels–Alder reaction betw...

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Veröffentlicht in:Tetrahedron letters 2014-12, Vol.55 (50), p.6864-6867
Hauptverfasser: Pigott, Adam J., Lepage, Romain J., White, Jonathan M., Coster, Mark J.
Format: Artikel
Sprache:eng
Schlagworte:
Cancer
Diels-Alder reactions
Diels–Alder reaction
Natural product
Natural products
Nicolaioidesin B
Nutrients
Panduratin A
Synthesis (chemistry)
Tetrahedrons
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Zusammenfassung:[Display omitted] The total synthesis of (±)-nicolaioidesin B, a natural product that shows preferential cytotoxicity against pancreatic cancer cells under nutrient starvation conditions, is achieved. The key step is a thermally-induced, highly regio- and diastereoselective Diels–Alder reaction between (E)-N-methoxy-N-methylcinnamide and ocimene under solvent-free conditions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.10.097