Helvetica Chimica Acta p. 2405 - 2418 (1981)
Update date:2022-08-04
Topics:
Widmer, Erich
Zell, Reinhard
Lukac, Teodor
Casadei, Marco
Schoenholzer, Peter
Broger, Emil A.
An efficient synthesis of (3S,3'S)-astaxanthin (1a) in high yield and optical purity starting from (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone (4) is reported.The absolute configuration of 1a, previously derived from ORD. data, has been confirmed by X-ray analysis of 5, a derivate of 6-oxo-isophorone (2).The key features of the improved synthesis are the two-step conversion of 4 to the key intermediate (4S)-2,6,6-trimethyl-4-hydroxy-2-cyclohexen-1-one (14), a new method for the partial reduction of the sterically hindered triple bond of (S)-6-hydroxy-3-(5-hydroxy-3-methyl-3-penten-1-ynyl)-2,4,4-trimethyl-2-cyclohexen-1-one (32), and Wittig olefination of the dialdehyde 1,6-dimethyl-1,3,5-octatrienedial (38) using phosphonium salt 37 with a free hydroxyl group.
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(1987)