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Synthese von optisch aktiven, natürlichen Carotinoiden und strukturell verwandten Naturprodukten. V. Synthese von (3 R , 3′ R )‐, (3 S , 3′ S )‐ und (3 R ,3′ S ; meso )‐Zeaxanthin durch asymmetrische Hydroborierung. Ein neuer Zugang zu Optisch aktiven Carotinoidbausteinen. Vorläufige Mitteilung
Author(s) -
Rüttimann August,
Mayer Hans
Publication year - 1980
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.19800630615
Subject(s) - chemistry , hydroboration , stereochemistry , optically active , zeaxanthin , enantioselective synthesis , carotenoid , organic chemistry , lutein , biochemistry , catalysis
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.