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Stereoselective Reduction of `Capsanthol‐3′‐ones' (=3,6′‐Dihydroxy‐ β , κ ‐caroten‐3′‐ones) by Complex Hydrides
Author(s) -
Deli József,
Ösz Erzsébet,
Visy Júlia,
Zsila Ferenc,
Simonyi Miklós,
Tóth Gyula
Publication year - 2001
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20010131)84:1<263::aid-hlca263>3.0.co;2-7
Subject(s) - chemistry , stereoselectivity , metal , mass spectrum , reduction (mathematics) , proton nmr , stereochemistry , spectral line , medicinal chemistry , organic chemistry , catalysis , ion , physics , astronomy , geometry , mathematics
The (3 R ,5′ R ,6′ R )‐ and (3 R ,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/VIS, CD, 1 H‐ and 13 C‐NMR, and mass spectra.