.beta.-lactams used in preparing taxol

Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...

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540354, 540360, C07D20508, C07D30514, C07C23387

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active

055741568

ABSTRACT:
A .beta.-lactam of the formula: ##STR1## wherein R.sub.1 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; R.sub.2 is hydrogen, alkyl, acyl, acetal, ethoxyethyl, or other hydroxyl protecting group; and R.sub.3 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; and the enantiomers and diastereomers thereof.

REFERENCES:
patent: 4680391 (1987-07-01), Firestone et al.
patent: 4814470 (1989-03-01), Colin et al.
patent: 4857653 (1989-08-01), Colin et al.
patent: 4924011 (1990-05-01), Denis et al.
patent: 4924012 (1990-05-01), Colin et al.
patent: 5105744 (1991-05-01), Holton
patent: 5136060 (1992-08-01), Holton
patent: 5175315 (1992-12-01), Holton
patent: 5254580 (1993-10-01), Chen et al.
patent: 5272171 (1993-12-01), Ueda et al.
patent: 5284864 (1994-02-01), Holton et al.
A. K. Mukerjee et al. "Synthesis of B-Lactams" Synthesis, No. 6, pp. 327-346 (1973).
A. K. Bose et al. "Studies on the Mechanism of B-lactam Formation" Tetrahedron Letters, No. 40, pp. 4091-4094 (1972).
A. K. Bose et al. "Studies on Lactams. Part XVI. Stereochemistry of B-lactam Formation" Tetrahedron Letters, No. 34, pp. 3167-3170 (1971).
T. W. Doyle et al. "Nuclear Analogs of B-lactam Antibiotics. I. Synthesis of O-2-isocephams" Canadian Jour. of Chemistry, vol. 55, pp. 468-483 (1977).
A. K. Bose et al. "Studies on B-lactams. XXXVI. Monocyclic Cis B-lactams via Penams and Cephams" Journal of Organic Chemistry, vol. 39, No. 19, pp. 2877-2884 (1974).
J. N. Wells et al. "The Synthesis of 2-Azetidinones" Journal of Organic Chemistry, vol. 34, No. 5, pp. 1477-1479 (1969).
A. K. Bose et al. "Studies on Lactams-V 3-Azido-2-Azetidinones" Tetrahedron Letters, vol. 23, pp. 4769-4776 (1967).
Hawley's Condensed Chemical Dictionary, 12th Ed., Van Nostrand Reinhold Co., pp. 21-22 (1993).
Zakhs et al. "Oxo Derivatives of 1,3-Oxazines" Chemistry of Heterocyclic Compounds, vol. 11 (1987) pp. 1147-1166.
Denis and Greene "A Highly Efficient, Practical Approach to Natural Taxol" Journal of American Chemical Society, vol. 110 (1988) pp. 5917-5919.
Holton et al. "A Synthesis of Taxusin" Journal of American Chemical Society, vol. 110 (1988) pp. 6558-6560.
Holton "Synthesis of the Taxane Ring System" Journal of American Chemical Society, vol. 106 (1984) pp. 5731-5732.
Ojima et al. "New and Efficient Approaches to the Semisynthesis of Taxol and its C-13 Side Chain Analogs by Means of B-Lactam Synthon Method" Tetrahedron Letters vol. 48, No. 34 (1992) pp. 6985-7012.
Bose et al. "Studies on Lactams-Vl 3j-Azido-2-Azetidinones" Tetrahedron Letters vol. 23 (1967) pp. 4769-4776.
Hart et al. "The Ester Enolate-Imine Condensation Route to .beta.-Lactams" Chemical Review, vol 38 (1989) pp. 1447-1465.
Mukerjee et al. ".beta.-Lactams: Retrospect and Prospect" Tetrahedron Letters vol. 34, No. 52 (1978) pp. 1731-1767.
Bartholomew et al. "A Novel Rearrangement Reaction Conversion of 3-(chloromethyl)azetidin-2-ones to Azetidine-3-carboxylic Acid Esters" Tetrahedron Letters, vol. 32, No. 36 (1991) pp. 4795-4798.
Schultz et al. "Synthesis of New N-radicals of Tetrazan-1-yl" Chemical Abstract, vol. 108, No. 37298C (1988) P. 581.
Steglich et al. "1,3-oxazin-6-ones: Versatile Intermediates In Heterocyclic Synthesis" Research Report, Gazzetta Chemica Italiana, 116 (1986) pp. 361-372.
Murkerjee "Reactions of Natural and Synthetic .beta.-Lactams" Synthesis (1975) pp. 547-590.
Kingston et al. "Progress in the Chemistry of Organic Natural Products" Springer Verlag, Wien New York (1993) pp. 145-150.
Evans et al. "The Asymmetric Synthesis of .beta.-lactam Antibotics-I. Application of Chiral Oxazolidones in the Staudinger Reaction" Tetrahedron Letters, vol. 26, No. 32 (1985) pp. 3783-3786.
Hart et al. "Asymmetric Synthesis of .beta.-lactams and the Carbapenem Antibiotic (+)-PS-5" Journal of American Chemical Society, vol. 108 (1986) pp. 6054-6056.
Burnett et al. "Synthesis of 3-(1-Hydroxyethyl)-2-azetidin-ones via Ester-Imine Condensations" Journal of Organic Chemistry, vol 50 (1989) pp. 5120-5123.
Cossia et al. "Triphenylphosphine Dibromide and Dimethyl-Sulfide Dibromide As Versatile Reagents For .beta.-Lactam Synthesis" Tetrahedron Letters, vol. 26, No. 25 (1985) pp. 3041-3044.
Georg et al. "Stereocontrolled Ketene-Imine Cycloaddition Reactions" The Organic Chemistry of .beta.-lactams, Chapter 6, pp. 295-368. (1982).
Cluchowski et al. "Preparation of .beta.-lactams by the Condensation of Lithium Ester Enolates With Aryl Aldimines", Journal of Organic Chemistry, vol. 45 (1980) pp. 3413-3416.
C. Palomo et al. "Highly Stereoselective Synthesis of .alpha.-Hydroxy .beta.-Amino Acids Through .beta.-Lactams: Application to the Synthesis of the Taxol and Bestatin Side Chains and Related Systems" Tetrahedron Letters, 31:44 (1990) pp. 6429-6432.

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