Premium
Synthese von Astaxanthin aus β‐Jonon. I. Erschliessung der enantiomeren C 15 ‐ Wittig salze durch chemische und mikrobiologische Racematspaltung von (±)‐3‐Acetoxy‐4‐oxo‐β‐jonon
Author(s) -
Becher Elisabeth,
Albrecht Robert,
Bernhard Kurt,
Leuenberger Hans G. W.,
Mayer Hans,
Müller Robert K.,
Schüep Willy,
Wagner Hans P.
Publication year - 1981
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/hlca.19810640750
Subject(s) - chemistry , wittig reaction , diastereomer , enantiomer , ionone , astaxanthin , alkylation , resolution (logic) , stereochemistry , organic chemistry , catalysis , carotenoid , food science , artificial intelligence , computer science
Synthesis of Astaxanthin from β‐Ionone. I. A Route to the Enantiomeric C 15 ‐ Wittig Salts by Chemical and Microbial Resolution of (±)‐3‐Acetoxy‐4‐oxo‐β‐ionone 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 diastereomeric 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° 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 [1].