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Synthese von optisch aktiven, natürlichen Carotinoiden und strukturell verwandten Naturprodukten. V. Synthese von (3R, 3′R)-, (3S, 3′S)- und (3R,3′S; meso)-Zeaxanthin durch asymmetrische Hydroborierung. Ein neuer Zugang zu Optisch aktiven Carotinoidbausteinen. Vorläufige Mitteilung

✍ Scribed by August Rüttimann; Hans Mayer

Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
384 KB
Volume
63
Category
Article
ISSN
0018-019X

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✦ Synopsis

Synthesis of Optically Active Natural Carotenoids and Structurally Related Compounds. V. Synthesis of (3__R__, 3′R)‐, (3__S__, 3′S)‐ and (3__R__,3′S; meso)‐zeaxanthin by Asymmetric Hydroboration. A New Approach to Optically Active Carotenoid Building Units

The synthesis of (3__R__, 3′R)‐, (3__S__, 3′S)‐ and (3__R__,3′S; meso)‐zeaxanthin (1), (19) and (21) is reported utilizing asymmetric hydroboration as the key reaction. Thus, safranol isopropenylmethylether (4) is hydroborated with (+)‐ and (−)‐(IPC)~2~BH to give the optically pure key intermediates 5 and 7 resp., which are transformed into the above‐mentioned C~40~‐compounds.

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