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

• Published in: Tetrahedron letters Vol. 55; no. 50; pp. 6864 - 6867
• Main Authors: Pigott, Adam J., Lepage, Romain J., White, Jonathan M., Coster, Mark J.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 10.12.2014; Elsevier
• Subjects: Cancer; Chemistry; Chemistry, Organic; Diels-Alder reactions; Diels–Alder reaction; Natural product; Natural products; Nicolaioidesin B; Nutrients; Panduratin A; Physical Sciences; Science & Technology; Synthesis (chemistry); Tetrahedrons; CIQQYRZTKOGULG-PQNGQFLHSA-N; Nicolaioidesin B; Panduratin A; QPASIUICYJHVJC-ICBNADEASA-N; OJSFFJVPKJOBSD-VAMGGRTRSA-N; Natural product; Diels–Alder reaction; Cancer; SECONDARY METABOLITES; APOPTOSIS; TOLERANCE; KAEMPFERIA-PANDURATA; INDUCTION; ANGELMARIN; NUTRIENT DEPRIVATION; PROSTATE-CANCER CELLS; Diels-Alder reaction; CYCLOHEXENYL CHALCONE DERIVATIVES; CONSTITUENTS

[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...