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Synthesis 2011(3): 509-516  
DOI: 10.1055/s-0030-1258382
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

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

Publication History

Received 17 October 2010
Publication Date:
23 December 2010 (online)

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Abstract

(3R)-3-Hydroxy-β-ionone and (3S)-3-hydroxy-β-ionone were synthesized in high enantiomeric purity from commercially available (±)-α-ionone. These ionones were then transformed into (3R)-β-cryptoxanthin and (3S)-β-cryptoxanthin by a C15+C10+C15 Wittig coupling strategy according to known methods. This methodology can considerably simplify the total synthesis of optically active carotenoids with 3-hydroxy-β-end groups that possess significant biological activities.

Key words

hydroxycarotenoids - carotenoid precursors - chiral resolution - stereoselective synthesis - Wittig reaction

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Current address: Martek Biosciences Corporation, 6480 Dobbin Road, Columbia, MD 21045, USA; E-mail: achang@martek.com.