Synthesis of symmetrical carotenoids by a two-fold Stille reaction.
beta-Carotene 1 and (3R,3'R)-zeaxanthin 2 have been stereoselectively prepared in a highly convergent fashion by a 2-fold Stille cross-coupling reaction. The C(12)-pentaenylbis-stannane 8 is the central "lynchpin" that connects two units of the terminal C(14)-iodides 9 and 17 to afford 1 and 2, respectively.
Vaz
Belén
B
Departamento de Química Orgánica, Facultad de Ciencias, Universidade de Vigo. 36200 Vigo, Spain.
Alvarez
Rosana
R
de Lera
Angel R
AR
D002338:Carotenoids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D007454:Iodides / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D017971:Tin Compounds / Q000737:chemistry*; D024341:Xanthophylls; D065146:Zeaxanthins; D019207:beta Carotene / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D007454:Iodides; D017971:Tin Compounds; D024341:Xanthophylls; D065146:Zeaxanthins; D019207:beta Carotene; D002338:Carotenoids