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Synthesis and Characterization of all ‐ E ‐(4,4′‐ 13 C 2 )‐Astaxanthin Strategies for Labelling the C 15 ‐End Groups of Carotenoids
Author(s) -
Jansen Frans Jos H. M.,
Lugtenburg Johan
Publication year - 2000
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/(sici)1099-0690(200003)2000:5<829::aid-ejoc829>3.0.co;2-z
Subject(s) - chemistry , phosphonium , synthon , astaxanthin , acetonitrile , phosphonium salt , salt (chemistry) , labelling , carotenoid , combinatorial chemistry , organic chemistry , biochemistry
The all ‐ E isomer of (4,4′‐ 13 C 2 )astaxanthin ( 1a ) has been prepared by total synthesis starting from commercially available 99% 13 C enriched acetonitrile. The labelled astaxanthin was obtained in high purity and with high isotope incorporation. For this synthesis, the C 15 + C 10 + C 15 strategy was used. The central C 10 ‐synthon, 2,7‐dimethylocta‐2,4,6‐triene‐1,8‐dial ( 3 ), was coupled with 13 C‐enriched C 15 ‐phosphonium salt 2a . The new synthetic scheme for the preparation of the C 15 ‐phosphonium salt is discussed in this paper; the same scheme can be used to label all positions and combinations of positions of the C 15 ‐phosphonium salt.