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Technische Verfahren zur Synthese von Carotinoiden und verwandten Verbindungen aus 6-Oxo-isophoron. III. Ein neues Konzept für die Synthese der enantiomeren Astaxanthine

✍ Scribed by Reinhard Zell; Erich Widmer; Teodor Lukáč; Hans Georg Wilhelm Leuenberger; Peter Schönholzer; Emil A. Broger

Publisher
John Wiley and Sons
Year
1981
Tongue
German
Weight
858 KB
Volume
64
Category
Article
ISSN
0018-019X

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✦ Synopsis

Technical Procedures for the Synthesis of Carotenoids and Related Compounds from 6‐Oxo‐isophorone. III. A New Concept for the Synthesis of the Enantiomeric Astaxanthins

A new and efficient concept for the total synthesis of (3__S__, 3'S)‐ and (3__R__, 3'R)‐astaxanthin (1a and 1c, resp.) in high overall yield and up to 99,2% enantiomeric purity is described. Key intermediates are the (S)‐ and (R)‐acetals 10 and 17, respectively (Scheme 2). These chiral building blocks were synthesized via three different routes: a) functionalization of the enantiomeric 3‐hydroxy‐6‐oxo‐isophorons^4^) 2 and 11, respectively (Scheme 2); b) optical resolution of 3,4‐dihydroxy‐compound^4^) 19 (Scheme 3), and c) fermentative reductions of 6‐oxo‐isophorone derivatives (Schemes 4 and 5). ‐ The absolute configurations of the two intermediates 12 and 13 (Scheme 2) have been confirmed by X‐ray analysis. ‐ The final steps leading to the enantiomeric astaxanthins are identical with those described for optically inactive astaxanthin [1].

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