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

Research output: Article

8 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)263-270
Number of pages8
JournalHelvetica Chimica Acta
Volume84
Issue number1
DOIs
Publication statusPublished - márc. 10 2001

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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