Reduction and resolution methods for the preparation of compound

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C07B 5500

Patent

active

058178678

ABSTRACT:
Reduction and resolution methods for the preparation of compounds useful as intermediates in the preparation of taxanes, and particularly for preparation of desired stereoisomers for use in the formation of the C-13 sidechain of pharmaceutically useful taxanes such as paclitaxel.

REFERENCES:
patent: 4584270 (1986-04-01), Sih
patent: 4656303 (1987-04-01), Kurono et al.
patent: 4800162 (1989-01-01), Matson
patent: 4814470 (1989-03-01), Colin et al.
patent: 4857468 (1989-08-01), Kutsuki et al.
patent: 4857653 (1989-08-01), Colin et al.
patent: 4876399 (1989-10-01), Holton et al.
patent: 4924011 (1990-05-01), Denis et al.
patent: 4924012 (1990-05-01), Colin et al.
patent: 5064761 (1991-11-01), Schneider et al.
patent: 5321154 (1994-06-01), Nohira
patent: 5420337 (1995-05-01), Patel et al.
patent: 5463106 (1995-10-01), Correa et al.
patent: 5567614 (1996-10-01), Patel et al.
Nakamura, et al., Stereoselective Preparation of (R)-4-Nitro-2-butanol and (R)-5-Nitro-2-pentanol Mediated by a Lipase; Agric. Biol. Chem., 54(6), pp. 1569-1570 (1990).
Kingston, The Chemistry of Taxol, Pharm. Ther., vol. 52, pp. 1-34 (1991).
Sih, et al., Mikrobielle asymmetrische Katalyze--enantioselektive Reduktion von Ketonen; Angew Chem., 96, pp. 556-565 (1984).
Georg, et al., Asymmetric Synthesis of .beta.-Lactams and N-Benzoyl-3-Phenylisoserines via the Staudinger Reaction, Tetrahedron Letters, vol. 32, No. 27, pp. 3151-3154 (1991).
Denis, et al., An Efficient, Enantioselective Synthesis of the Taxol Side Chain, J. Org. Chem., 51, pp. 46-50 (1986).
Honig, et al., Chemo-Enzymatic Synthesis of All Isomeric 3-Phenylserines and -Isoserines, Tetrahedron, vol. 46, No. 11, pp. 3841-3850 (1990).
Fones, The Isomers of the .beta.-phenylserines, J. Biol. Chem., 204, pp. 323-328 (1953).
Denis, et al., An Improved Synthesis of the Taxol Side Chain and of RP 56976; J. Org. Chem., 55, pp. 1957-1959 (1990).
Ojima, et al., Efficient and Practical Asymmetric Synthesis of the Taxol C-13 Side Chain, N-Benzoyl-(2R,3S)-3-phenylisoserine, and Its Analogues via Chiral 3-Hydroxy-4-aryl-.beta.-lactams through Chiral Ester Enolate-Imine Cyclocondensation, J. Org. Chem., 56, pp. 1681-1683 (1991).
Imuta, et al., Product Stereospecificity in the Microbial Reduction of .alpha.-Haloaryl Ketones, J. Org. Chem., 45, pp. 3352-3355 (1980).
Ohta, et al., Microbial Reduction of 1,2-Diketones to Optically Active .alpha.-Hydroxyketones; Agric. Biol. Chem., 51(9), pp. 2421-2427 (1987).
Hummel, Reduction of acetophenone to R(+)-phenylethanol by a new alcohol dehydrogenase from Lactobacillus kefir; Appl. Microbial Biotechnol, 34, pp. 15-19 (1990).
Shen, et al., A New NAD-dependent Alcohol Dehydrogenase with Opposite Facial Selectivity useful for Asymmetric Reduction and Cofactor Regeneration, J. Chem. Soc., Chem. Commun., pp. 677-679 (1990).
Christen, et al., Biotransformation in Organic Synthesis: Applications of Yeast Reduction in the Synthesis of 3,5-Dihydroxy Esters of High Optical Purity, J. Chem. Soc., Chem. Commun., pp. 264-266 (1988).
Fujisawa, et al., Diastereo- and Enantioselective Reduction of .alpha.,.beta.-Diketodithiane with the Baker's Yeast, Tetrahedron Letters, vol. 26, No. 49, pp. 6089-6092 (1985).
Willaert, et al., Enzymatic in Vitro Reduction of Ketones; Bioorganic Chemistry, pp. 223-231 (1988).
Hoffmann, et al., Synthesis of 6S,7S-Anhydro-Serricornine, Tetrahedron Letters, vol. 23, No. 34, pp. 3479-3482 (1982).
Bernardi, et al., Production of (R)-1-(1,3-Dithian-2-yl)propan-2-ol by Microbial Reduction; J. Chem. Soc., Perkin Trans. I, pp. 1607-1608 (1987).
Chunduru, et al., Mechanism of Ketol Acid Reductoisomerase--Steady-State Analysis and Metal Ion Requirement, Biochemistry, vol. 28, No. 2, pp. 486-493 (1989).
Utaka, et al., Asymmetric Reduction of a Prochiral Carbonyl Group of Aliphatic .gamma.-and .delta.-Keto Acids by Use of Fermenting Bakers' Yeast, J. Org. Chem., vol. 52, pp. 4363-4368 (1987).
Dale, et al., .alpha.-Methoxy-.alpha.-trifluoromethylphenylacetic Acid, a Versatile Reagent for the Determination of Enantiomeric Composition of Alcohols and Amines; The J. of Org. Chem., vol. 34, No. 9, pp. 2543-2550 (1969).
Naoshima, et al., Biotransformation of Some Keto Esters through the Consecutive Reuse of Immobilized Nicotiana tabacum Cells; J. Org. Chem., vol. 54, pp. 4237-4239 (1989).
Bucciarelli, et al., Asymmetric Reduction of Trifluoromethyl and Methyl Ketones by Yeast; An Improved Method; Synthesis Communications, pp. 897-899 (1983).
Charles, et al., Bicyclic Heterocycles with Nitrogen at the Ring Junction. Part 2. Application of the Dakin-West Reaction to the Synthesis of (1980).
Denis, et al., A Highly Efficient, Practical Approach to Natural Taxol, J. Am. Chem. Soc., 110, 5917-5919 (1988).
Deng et al., A Practical, Highly Enantioselective Synthesis of the Taxol Side Chain via Asymmetric Catalysis; J. Org. Chem., 57, pp. 4320-4323 (1992).
Holton, et al., A Synthesis of Taxusin, J. Am. Chem. Soc., 110, pp. 6558-6560 (1988).
Angelastro et al., .alpha.-Diketone and .alpha.-Keto Ester Derivatives of N-Protected Amino Acids and Peptides as Novel Inhibitors of Cysteine and Serine Proteases, J. Med. Chem., 33(1), pp. 11-13 (1990).
Magri et al., Modified Taxols. 2. Oxidation Products of Taxol, J. Org. Chem., 51(6), pp. 797-802 (1986).
Battersby et al., J. Chem Soc., Perkin Trans., 1(9), 1565-1580 (1986) (also, Chemical Abstracts 107:217326).
Blinnikova et al., Izv. Timiryazevsk. S-kh. Akad., (6) 195-201 (1990) (also, Chemical Abstracts 114:185430d).
Saus et al., Chem.-Ztg. 115(9), 252-253 (1991) (also, Chemical Abstracts 115:279402u).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Reduction and resolution methods for the preparation of compound does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Reduction and resolution methods for the preparation of compound, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Reduction and resolution methods for the preparation of compound will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-79848

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.