We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Synthese von optisch aktiven, natürlichen Carotinoiden und strukturell verwandten Naturprodukten. I. Synthese der chiralen Schlüsselverbindung (4 R, 6 R)-4-Hydroxy-2,2,6-trimethylcyclohexanon.
- Authors
Leuenberger, Hans Georg Wilhelm; Boguth, Walter; Widmer, Erich; Zell, Reinhard
- Abstract
Synthesis of optically active natural carotenoids and structurally related compounds. I. Synthesis of the chiral key compound (4 R, 6 R)-4-hydroxy-2,2,6-trimethylcyclohexanone. A technical synthesis of (4 R, 6 R)-4-hydroxy-2,2,6-trimethylcyclohexanone ( 7) starting from the readily available oxo-isophorone ( 2) is described. 7 is an ideal precursor for the synthesis of naturally occurring, optically active hydroxylated carotenoids ( e.g. zeaxanthin, cryptoxanthin and structurally related compounds). Chirality is introduced at C(6) by a stereoselective fermentative hydrogenation of the double bond using baker's yeast as the biocatalyst. Thereafter the carbonyl group at C(4) is reduced selectively and stereospecifically by chemical methods to the corresponding alcohol. Chemical reduction is preferably carried out by hydrogenation in the presence of a nickel catalyst or using triisobutylaluminium as the reducing agent. Stability, stereochemistry and physical properties of 7 and the stereoisomers thereof are discussed.
- Publication
Helvetica Chimica Acta, 1976, Vol 59, Issue 5, p1832
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19760590541