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

被引：1
|
作者：
Khachik, Frederick [1 ]
机构：
[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA
来源：
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 03期
关键词：
optically active hydroxycarotenoids; partial synthesis; chiral resolution; regioselective hydroboration; highly conjugated polyenes; STRUCTURALLY RELATED-COMPOUNDS; ACTIVE NATURAL CAROTENOIDS; HUMAN PLASMA; TECHNICAL PROCEDURES; DIETARY CAROTENOIDS; OXIDATION-PRODUCTS; ALPHA-PINENE; ZEAXANTHIN; LUTEIN; IDENTIFICATION;
D O I：
10.1055/s-0031-1289662
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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-beta, beta-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 mesoisomer accumulate in human ocular tissues and have been implicated in the prevention of age-related macular degeneration (AMD).
引用
收藏
页码：453 / 459
页数：7
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