Preparation of zeaxanthin, intermediates for this preparation, a

Details Preparation of zeaxanthin, intermediates for this preparation, a Preparation of zeaxanthin, intermediates for this preparation, a

1998-06-04

2000-08-15

Owens, Amelia

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

568 9, 568 11, 549459, C07C 3518

Patent

active

061039403

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

REFERENCES:
patent: 2521113 (1950-09-01), Braconier et al.
patent: 3988205 (1976-10-01), Boguth et al.
patent: 4134922 (1979-01-01), Leeder
patent: 4177126 (1979-12-01), Doorakian et al.
patent: 4225527 (1980-09-01), Bollag et al.
patent: 5504230 (1996-04-01), John et al.
CA 126:19071, 1996.
CA 122:133469, 1995.
CA 107:134225, 1987.
CA 106:156186, 1986.
August Ruettimann, et al., Helvetica Chemical Acta, vol. 63, pp. 1456-1462, "Synthese Von Optisch Aktiven, Natuerlichen Carotinoiden Und Strkturell Verwandten Naturproducten", 1980.
Hiroaki Taguchi, et al., Tetrahedron Letters, No. 27, pp. 2465-2468, "A New Synthesis of Alpha, Beta-Unsaturated Aldehydes Including (E)2-Methyl-2-Alkenal", 1973.
Widmer, et al. "Technical Procedures for the Syntheses of Carotenoids and Related Compounds from 6-Oxo-isophorone: Syntheses of (3R,3'R)-Zeaxathin,", Helvetica Chimica Acta, vol. 73, (1990), pp. 861-867.
Soukup, et al. "Technical Procedures for the Syntheses of Carotenoids and Related Compounds from 6-Oxo-isophorone: Syntheses of (3R,3'R)-Zeaxanthin Part II", Helv. Chimica Acta, vol. 73, (1990), pp. 868-873.
Taguchi, et al. "A New Synthesis of .alpha.,.beta.-Unsaturated Aldehydes Including (E)2-Methyl-2-Alkenal", Tetrahedron Letters No. 27, (1973), pp. 2465-2468.
Ramsay, "Intensities and Shapes of Infrared Absorption Bands of Substances in the Liquid Phase", The Journal of the American Chemical Society, vol. 74, Jan.-Mar. (1952), pp. 72-80.
Oroshnik, et al. "Synthesis of Polyenes. I. Retrovitamin A Methyl Ether. Spectral Relationships between the .beta.-Ionylidene and Retroionylidene Series, " The Journal of the American Chemical Society, vol. 295, Jan.-Mar. (1952) pp. 295-304.
Schlittler, et al, "Uber die Alkaloide aus Strychnos melinoniana Baillon ", Helvetica Chimica Acta, vol. 35, (1952), pp. 29-45.
Schindler, et al. "Identifizierung von Substanz Nr. 763 aus Strophanthus speciosus und S. Boivinii als Strospesid (Desgluco-digitalinum-verum)", Helvetica Chimica Acta, vol. 35, No. 56 (1952), pp. 442-447.
Ishikawa, "The Synthesis of .beta.-Ionylideneacetaldehyde" Bulletin of the Chemical Society of Japan, vol. 37, No. 2 (1964), pp. 207-209.
Torii, et al., "Electrooxidative Cleavage of Carbon--Carbon Linkages. 1. Preparation of Acyclic Oxoalkanoates from 2-Hydroxy- and 2-Acetoxy-1-cycloalkanones and Cycloalkanone Enol Acetates", The Journal of Organic Chemistry, vol. 47, No.1 (1982), pp. 47-52.
Rosenberger, et al., "Canthaxanthin. A New Total Synthesis", The Journal of Organic Chemistry, vol. 47, No. 11 (1982), pp. 2130-2134.
Ruttimann, et al., "Synthese von optisch aktiven, naturlichen Carotinoiden und strukturell verwandten Naturprodukten V. Synthese von (3R, 3'R)-, (3S, 3'S)-und (3R, 3'S; meso)-Zeaxanthin durch asymmetrische Hydroborierung. Ein neuer Zugang zu optisch aktiven Carotinoidbausteinen", Helvetica Chimica Acta, vol. 63, No. 154 (1980), pp. 1456-1462.
Chemical Abstracts, vol. 112, No. 7, Feb. 12, 1990, AN 54986a, DD 267,629, May 10, 1989.
Chemical Abstracts, vol. 112, No. 7, Feb. 12, 1990, AN 54987b, DD 265, 289, Mar. 1, 1989.
Chemical Abstracts, vol. 69, No. 26, Dec. 23, 1968, AN 108210g, U.S.S.R 220,957, Jul. 1, 1968.
Chemical Abstracts, vol. 119, No. 22, Nov. 29, 1993, AN 231586n, Hideki Nagata, et al., "Analytical Study of the Formation of Hemimorphite. I. Analysis of the Crystallization Process by the Co-Precipitation Method".
Chemical Abstracts, vol. 72, No. 6, Feb. 9, 1970, AN 27871h, A. G. Merkulov, et al., "Low-Temperature Synthesis of Zinc Silicates".
Chemical Abstracts, vol. 102, No. 24, Jun. 17, 1985, AN 206083n, JP 60-11219, Jan. 21, 1985.

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