Helvetica Chimica Acta p. 861 - 867 (1990)
Update date:2022-08-05
Topics:
Widmer, Erich
Soukup, Milan
Zell, Reinhard
Broger, Emil
Wagner, Hans Peter
Imfeld, Marquard
Starting from the readily available, optically active (4R)-4-hydroxy-2,2,6-trimethylcyclohexanone (1), a new technical synthesis of (3R,3'R)-zeaxanthin is described.According to a 2(C9 + C6) + C10= C40 construction scheme, the ketone 1 was first transformed with (E)-3-methylpent-2-en-4-yn-1-ol (5) into a C15-intermediate which, by a three-step sequence, could be converted into the known olefinic C15-Wittig salt 4.Optimized conditions for the final Wittig reaction of 4 with the C10-dialdehyde 3 are discussed.Based on 1, the overall yield of the entire technical process is ca. 40percent.
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Doi:10.1002/adsc.201000888
(2011)Doi:10.1021/ol2010193
(2011)Doi:10.1039/c0ob01248c
(2011)Doi:10.1016/j.ejmech.2011.02.071
(2011)Doi:10.1016/j.bmcl.2011.03.045
(2011)Doi:10.1016/S0957-4166(00)86314-4
(1990)
