Convergent stereoselective synthesis of the visual pigment A2E.
[chemical reaction: see text]. A stereoselective total synthesis of the visual pigment A2E has been achieved with use of palladium-catalyzed cross-coupling reactions in all key steps: a regioselective Suzuki or Negishi coupling of 2,4-dibromopyridine, a Sonogashira reaction, and a double Stille cross-coupling to complete the bispolyenyl skeleton.
Sicre
Cristina
C
Departamento de Química Orgánica, Universidade de Vigo, Campus Lagoas-Marcosende, 36310 Vigo, Spain.
Cid
M Magdalena
MM
D002384:Catalysis; D004396:Coloring Agents / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011726:Pyridinium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012176:Retinoids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C112040:A2-E (N-retinylidene-N-retinylethanolamine); D004396:Coloring Agents; D011726:Pyridinium Compounds; D012176:Retinoids; D010165:Palladium