Stereoselective reduction of 'capsanthol-3′-ones' (= 3,6′-dihydroxy-β,κ-caroten-3′-ones) by complex hydrides

TitleStereoselective reduction of 'capsanthol-3′-ones' (= 3,6′-dihydroxy-β,κ-caroten-3′-ones) by complex hydrides
Publication TypeJournal Article
Year of Publication2001
AuthorsDeli, J, Osz, E, Visy, J, Zsila, F, Simonyi, M, Tóth, G
JournalHelvetica Chimica Acta
Volume84
Issue1
Pagination263 - 270
Date Published2001
Abstract

The (3R.5′ R.6'′ R)-and(3R,5′R.6′S)-capsanthol-3′-one (= 3.6′-dihydroxy-β-κ-caroten-3′-one: 4 and 5. resp.) were reduced by different complex metal hydrides containing organic ligands. The ratio of the thus obtained diastereoisomeric (3′S)-capsanthols 2 and 3 or (3′R)-capsanthols 6 and 7, respectively, was investigated. Four complex hydrides showed remarkable stereoselectivity and produced the (3′R,6′S)-capsanthol (6) in 80-100% (see Table 1). The starting materials and the products were characterized by UV/V1S, CD, 1H- and 13C-NMR, and mass spectra.

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