Preparation of zeaxanthin, intermediates for this preparation, and the preparation thereof

作者: Wolfgang Kriegl , Joachim Paust

DOI:

关键词: Medicinal chemistrySalt (chemistry)Organic chemistryLithium diisopropylamideZeaxanthinArylDichloromethaneHeptaneKetoneButyllithiumChemistry

摘要: Preparing (3R, 3'R)-zeaxanthin of the formula I ##STR1## starting from (4-hydroxy-2,2,6-trimethylcyclohexanone II ##STR2## via novel intermediates (4R,6R)-1-formyl-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptane IV ##STR3## (4R,6R)-1-(3-oxo-1-butenyl)-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptane V ##STR4## (4R,6R)-1-(3-hydroxy-3-methyl-1,4-pentadienyl)-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptane VI ##STR5## [5-(4R,6R)-(4-hydroxy-2,2,6-trimethyl-1-cyclohexylidene)-3-methyl-1,3-pentadienyl]triarylphosphonium salt iso-III ##STR6## where Ar is aryl and X one equivalent an anion a strong acid. The obtained by reacting ketone with dichloromethyllithium, which can be prepared metallation dichloromethane butyllithium or lithium diisopropylamide.

参考文章(19)
E. Schlittler, J. Hohl, Über die Alkaloide aus Strychnos melinoniana Baillon Helvetica Chimica Acta. ,vol. 35, pp. 29- 45 ,(1952) , 10.1002/HLCA.19520350103
Hans Georg Wilhelm Leuenberger, Erich Widmer, Walter Boguth, Hans Johann Mayer, Reinhard Zell, Optically active cyclohexane derivatives ,(1976)
Hiroaki Taguchi, Shin Tanaka, Hisashi Yamamoto, Hitosi Nozaki, A new synthesis of α,β-unsaturated aldehydes including (e)2-methyl-2-alkenal Tetrahedron Letters. ,vol. 14, pp. 2465- 2468 ,(1973) , 10.1016/S0040-4039(01)96179-9
Yozo Ishikawa, The Synthesis of β-Ionylideneacetaldehyde Bulletin of the Chemical Society of Japan. ,vol. 37, pp. 207- 209 ,(1964) , 10.1246/BCSJ.37.207
Michael Rosenberger, Patrick McDougal, Julie Bahr, Canthaxanthin. A new total synthesis Journal of Organic Chemistry. ,vol. 13, pp. 2130- 2134 ,(1982) , 10.1021/JO00132A028
Erich Widmer, Milan Soukup, Reinhard Zell, Emil Broger, Hans Peter Wagner, Marquard Imfeld, Technical Procedures for the Syntheses of Carotenoids and Related Compounds from 6‐Oxo‐isophorone: Syntheses of (3R,3′R)‐Zeaxanthin. Part I Helvetica Chimica Acta. ,vol. 73, pp. 861- 867 ,(1990) , 10.1002/HLCA.19900730411
Joachim Paust, Michael John, Preparation of 13-(Z)-retinoic acid ,(1994)
Erich Dr. Widmer, Teodor Lukàc, Milan Dr. Soukup, Process for the preparation of pentadienol derivatives ,(1984)
Jean Dawance, Albert Braconier Frederic Fran, Process for the synthesis of vinyl esters of carboxylic acids ,(1948)