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Synthesis of C 40 ‐Symmetrical Fully Conjugated Carotenoids by Olefin Metathesis
Author(s) -
Fontán Noelia,
Domínguez Marta,
Álvarez Rosana,
de Lera Ángel R.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100935
Subject(s) - chemistry , conjugated system , dichloromethane , olefin fiber , olefin metathesis , metathesis , carotenoid , lycopene , zeaxanthin , catalysis , grubbs' catalyst , organic chemistry , stereochemistry , lutein , solvent , polymerization , biochemistry , polymer
In an effort to push olefin metathesis to the limits of conjugation in reactants and products, the C 40 ‐symmetrical carotenoids β,β‐carotene ( 1 ), lycopene ( 2 ), (3 R ,3′ R )‐zeaxanthin ( 3 ), and rac ‐isozeaxanthin ( 4 ), which are conjugated undecaenes, have been synthesized from C 21 ‐terminal hexaenes by treatment with Grubbs' second‐generation Ru catalyst in dichloromethane at 50 °C.