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Synthesis 2012(3): 453-459  
DOI: 10.1055/s-0031-1289662
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (3R,3′R)-Zeaxanthin and Its meso-Stereoisomer from (3R,3′R,6′R)-Lutein via (3R)-3′,4′-Anhydrolutein

Frederick Khachik*
Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA
Fax: +1(301)3149121; e-Mail: khachik@umd.edu;
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Publikationsverlauf

Received 28 October 2011
Publikationsdatum:
02. Januar 2012 (online)

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Abstract

A process has been developed for the partial synthesis of (3R,3′R)-zeaxanthin and (3R,3′S; meso)-zeaxanthin from commercially available (3R,3′R,6′R)-lutein. This involves the regioselective hydroboration of a dehydration product of lutein, namely (3R)-3′,4′-didehydro-β,β-caroten-3-ol [(3R)-3′,4′-anhydrolutein], to yield a mixture of (3R,3′R)-zeaxanthin and (3R,3′S; meso)-zeaxanthin followed­ by separation of these carotenoids by enzyme-mediated acylation. (3R,3′R,6′R)-Lutein, (3R,3′R)-zeaxanthin and its meso-isomer accumulate in human ocular tissues and have been implicated in the prevention of age-related macular degeneration (AMD).

Key words

optically active hydroxycarotenoids - partial synthesis - chiral resolution - regioselective hydroboration - highly conjugated polyenes

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