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Total synthesis of (3R,3'R,6'R)-lutein and its stereoisomers.
J Org Chem. 2009 May 15; 74(10):3875-85.JO

Abstract

(3R,3'R,6'R)-lutein (1) is a major dietary carotenoid that is abundant in most fruits and vegetables commonly consumed in the U.S. and that accumulates in the human plasma, major organs, and ocular tissues. Numerous epidemiological and experimental studies have shown that 1 has important biological activities and may play an important role in the prevention of age-related macular degeneration (AMD). While the total synthesis of 1 has been previously reported in a poor overall yield, the total synthesis of the other seven stereoisomers of lutein has not yet been accomplished. We have developed a relatively straightforward methodology for the total synthesis of 1 and three of its stereoisomers, (3R,3'S,6'S)-lutein (2), (3R,3'S,6'R)-lutein or 3'-epilutein (3), and (3R,3'R,6'S)-lutein (4) by C(15) + C(10) + C(15) Wittig coupling reactions. Employing this methodology, the other four stereoisomers of lutein that are enantiomeric to the aforementioned lutein isomers can be similarly prepared. One of the important features of this strategy is its application to the total synthesis of (13)C-labeled luteins and their metabolites with appropriate stereochemistry for metabolic studies in animals and humans. This synthesis also provides access to the C(15)-precursors of optically active carotenoids with a 3-hydroxy-epsilon end group that are otherwise difficult to synthesize.

Authors+Show Affiliations

Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA. khachik@umd.eduNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

19391613

Citation

Khachik, Frederick, and An-Ni Chang. "Total Synthesis of (3R,3'R,6'R)-lutein and Its Stereoisomers." The Journal of Organic Chemistry, vol. 74, no. 10, 2009, pp. 3875-85.
Khachik F, Chang AN. Total synthesis of (3R,3'R,6'R)-lutein and its stereoisomers. J Org Chem. 2009;74(10):3875-85.
Khachik, F., & Chang, A. N. (2009). Total synthesis of (3R,3'R,6'R)-lutein and its stereoisomers. The Journal of Organic Chemistry, 74(10), 3875-85. https://doi.org/10.1021/jo900432r
Khachik F, Chang AN. Total Synthesis of (3R,3'R,6'R)-lutein and Its Stereoisomers. J Org Chem. 2009 May 15;74(10):3875-85. PubMed PMID: 19391613.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Total synthesis of (3R,3'R,6'R)-lutein and its stereoisomers. AU - Khachik,Frederick, AU - Chang,An-Ni, PY - 2009/4/28/entrez PY - 2009/4/28/pubmed PY - 2009/7/22/medline SP - 3875 EP - 85 JF - The Journal of organic chemistry JO - J. Org. Chem. VL - 74 IS - 10 N2 - (3R,3'R,6'R)-lutein (1) is a major dietary carotenoid that is abundant in most fruits and vegetables commonly consumed in the U.S. and that accumulates in the human plasma, major organs, and ocular tissues. Numerous epidemiological and experimental studies have shown that 1 has important biological activities and may play an important role in the prevention of age-related macular degeneration (AMD). While the total synthesis of 1 has been previously reported in a poor overall yield, the total synthesis of the other seven stereoisomers of lutein has not yet been accomplished. We have developed a relatively straightforward methodology for the total synthesis of 1 and three of its stereoisomers, (3R,3'S,6'S)-lutein (2), (3R,3'S,6'R)-lutein or 3'-epilutein (3), and (3R,3'R,6'S)-lutein (4) by C(15) + C(10) + C(15) Wittig coupling reactions. Employing this methodology, the other four stereoisomers of lutein that are enantiomeric to the aforementioned lutein isomers can be similarly prepared. One of the important features of this strategy is its application to the total synthesis of (13)C-labeled luteins and their metabolites with appropriate stereochemistry for metabolic studies in animals and humans. This synthesis also provides access to the C(15)-precursors of optically active carotenoids with a 3-hydroxy-epsilon end group that are otherwise difficult to synthesize. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19391613/Total_synthesis_of__3R3'R6'R__lutein_and_its_stereoisomers_ L2 - https://dx.doi.org/10.1021/jo900432r DB - PRIME DP - Unbound Medicine ER -