42273-19-8Relevant articles and documents
Synthetic Sulfur Carotenoids II: Optically Active Carotenoid Thiols
Sliwka, Hans-Richard,Liaaen-Jensen, Synnoeve
, p. 361 - 368 (1993)
(3R,3'R)-Zeaxanthin was reacted with thioacetic acid or with thiocyano acid in a Mitsunobu reaction to provide the corresponding thioacetates and thiocyanates with inverted configuration.Reduction or hydrolysis of these intermediates provided (3R,3'S)-3'-
Synthetic Nitrogen Carotenoids: Optically Active Carotenoid Amines
Sliwka, Hans-Richard,Liaaen-Jensen, Synnove
, p. 2377 - 2382 (2007/10/02)
(3R,3'R)-Zeaxanthin was reacted with hydrazoic acid in a Mitsonobu reaction to yield azides with inverted configuration.Reduction of these azides with hydrogen telluride provided (3S)-2',3'-didehydro-β,β-caroten-3-amine, (3R,3'S)-3'-amino-β,β-caroten-3-ol
Partial Syntheses of Diastereomeric Carotenols
Sliwka, Hans-Richard,Liaaen-Jensen, Synnoee
, p. 518 - 525 (2007/10/02)
The application of the Mitsunobu reaction was successfully tested on (3R,3'R)-zeaxanthin, giving the (3S,3'S)-enantiomer and meso form.Applied to natural (3R,3'R,6'R)-lutein, this inversion reaction allowed the preparation of the three other 6'R diastereomers. (3S,3'S,6'R)-lutein with 3',6'-cis-configuration of the ε-ring has not been synthesized before.The observed Cotton effects of the eight lutein diastereomers are rationalized by application of the additivity hypothesis.New trivial names are suggested for the eight lutein isomers on the basis of structural relationships.