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Synthesis 2014; 46(05): 635-645
DOI: 10.1055/s-0033-1340555
paper
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of 1,2,5,6-Tetrahydro-2,6-cyclo-γ-carotene-1,5-diol, an Oxidation Product of γ-Carotene

Kristine Crawford
a   Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA   Fax: +1(301)3149121   Email: khachik@umd.edu
b   DSM Nutritional Products, 6480 Dobbin Rd., Columbia, MD 21045, USA
,
Eugene Mazzola
a   Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA   Fax: +1(301)3149121   Email: khachik@umd.edu
c   Joint Institute for Food Safety and Applied Nutrition (JIFSAN), Food and Drug Administration, College Park, MD 20742, USA
,
Frederick Khachik*
a   Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA   Fax: +1(301)3149121   Email: khachik@umd.edu
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Further Information

Publication History

Received: 04 November 2013

Accepted after revision: 10 December 2013

Publication Date:
21 January 2014 (online)

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Abstract

1,2,5,6-Tetrahydro-2,6-cyclo-γ-carotene-1,5-diol, an oxidation product of the pro-vitamin A food carotenoid γ-carotene, was synthesized by a C15 + C10 + C15 double Wittig coupling strategy. The total synthesis involved a key C15-dihydroxyaldehyde synthon derived from (E/Z)-citral, a protected C10-Wittig salt, and (β-ionylideneethyl)triphenylphosphonium chloride (C15-Wittig salt). This synthetic route provides novel access to an oxidation product of γ-carotene that could be potentially formed in humans or biological systems as a consequence of metabolic oxidation.

Key words

hydroxycarotenoids - Wittig reaction - γ-carotene oxidation - carotenoid precursors - epoxide cyclization