Synthese von Astaxanthin aus β-Jonon. I. Erschliessung der enantiomeren C15-Wittigsalze durch chemische und mikrobiologische Racematspaltung von (+/-)-3-Acetoxy-4-oxo-β-jonon
Racemic 3-acetoxy-4-oxo-β-ionone (10) was synthesized from the industrially accessible intermediate β-ionone (5).Resolution of 10 into its enantiomers was achieved via the corresponding diastereometric camphanates and by microbial resolution.Site-selective alkylation of racemic and of optically pure 3-acyloxy-4-oxo-β-ionones with vinyl magnesium chloride at -70 deg furnished the corresponding 3-acyloxy-4-oxo-9-vinyl-β-ionols which could be transformed to the Wittig salts 1, 3 and 4, respectively, following known procedures .
Becher, Elisabeth,Albrecht, Robert,Bernhard, Kurt,Leuenberger, Hans G. W.,Mayer, Hans,et al.
p. 2419 - 2435
(2007/10/02)
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