Synthesis of (3S)- and (3R)-3-Hydroxy-β-ionone and Their Transformation into (3S)- and (3R)-β-Cryptoxanthin

被引：12
|
作者：
Khachik, Frederick [1 ]
Chang, An-Ni [1 ]
机构：
[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA
来源：
SYNTHESIS-STUTTGART | 2011年 / 03期
关键词：
hydroxycarotenoids; carotenoid precursors; chiral resolution; stereoselective synthesis; Wittig reaction; STRUCTURALLY RELATED-COMPOUNDS; ACTIVE NATURAL CAROTENOIDS; TECHNICAL PROCEDURES; BETA-CRYPTOXANTHIN; (3R; 3'R)-ZEAXANTHIN; 3'R; 6'R)-LUTEIN; 6-OXO-ISOPHORONE; ZEAXANTHIN; TISSUES; RHODOXANTHIN;
D O I：
10.1055/s-0030-1258382
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(3R)-3-Hydroxy-beta-ionone and (3S)-3-hydroxy-beta-ionone were synthesized in high enantiomeric purity from commercially available (+/-)-alpha-ionone. These ionones were then transformed into (3R)-beta-cryptoxanthin and (3S)-beta-cryptoxanthin by a C(15)+C(10)+C(15) Wittig coupling strategy according to known methods. This methodology can considerably simplify the total synthesis of optically active carotenoids with 3-hydroxy-beta-end groups that possess significant biological activities.
引用
收藏
页码：509 / 516
页数：8
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