Method of making asymmetric DE ring intermediates for the synthe

Details Method of making asymmetric DE ring intermediates for the synthe Method of making asymmetric DE ring intermediates for the synthe

1995-02-07

1996-03-05

Dentz, Bernard

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546342, C07D491052, C07D21355

Patent

active

054969522

ABSTRACT:
The present invention is directed towards new methods of making DE ring intermediates of Formula (III), ##STR1## wherein Y is H or halogen and R is loweralkyl, which in turn are useful in methods of making camptothecin and camptothecin analogs. The present invention also provides new compounds useful in the methods of making compounds of Formula (III).

REFERENCES:
patent: 4578381 (1986-03-01), Uchida et al.
patent: 4894456 (1990-01-01), Wall et al.
patent: 5162532 (1992-11-01), Comins et al.
patent: 5191082 (1993-03-01), Comins et al.
patent: 5212317 (1993-05-01), Comins et al.
patent: 5243050 (1993-09-01), Comins et al.
patent: 5342947 (1994-08-01), Lackey et al.
Comins, D. L., et al., Lithiation of Methoxypyridines Directed by .alpha.-Amino Alkoxides, The Journal of Organic Chemistry, 55 (1) p. 69 (1990).
Comins, D. L., Ortho Lithiation of 2-,3-, and 4-Methoxypyridines, Tetrahedron Letters, 29 (7) p. 773 (1988).
Lyle, R. E., et al., Synthetic Approaches to Camptothecin, Abstracts, 23rd International Congress of Pure and Applied Chemistry, Abstracts, p. 67 (1971).
Lyle, R. E., et al., The Synthesis of an Analog of Camptothecin by a General Method, The Journal of Organic Chemistry, 38 (19) p. 3268 (1973).
Comins, D. L., et al., Ortho Metalation Directed by .alpha.-Amino Alkoxides, The Journal of Organic Chemistry, 49: p. 1078 (1984).
Comins, D. L., et al., Ortho Substitution of m-Anisaldehyde via .alpha.-Amino Alkoxide Directed Lithiation, The Journal of Organic Chemistry, 54: p. 3730 (1989).
Bristol, J. A., et al., Analogs of Camptothecin, The Journal of Medicinal Chemistry, 18 (5) p. 535 (1975).
Abramovitch, Pyridine and Its Derivatives, Heterocyclic Compounds, Suppl. Pt. 3., 14: p. 745 (1982).
Sugasawa, T., et al., Experiments on the Synthesis of dl-Camptothecin. II.-Synthesis of a D-E Ring Analog of Camptothecin and a Total Synthesis of Ricinine, Chem. Pharm. Bull., 22 p. 763 (1974).
Plattner, J. J., et al., Synthesis of Some DE and CDE Ring Analogs of Camptothecin, The Journal of the American Chemical Society, 94:24: p. 8613 (1972).
Cai, J. Camptothecin, The Alkaloids, 21 p. 101 (1983).
Comins, D. L., A 10-Step Asymmetric Synthesis of (S)-Campothecin, Journal of the American Chemical Society, p. 10971 (1992).
Comins, D. L., Ph.D. Thesis, University of New Hampshire, Durham, New Hampshire pp. 25-29 (1977).
Lyle, Robert E. et al; Benzylic Halogenation of Methylquinolines, The Journal of Organic Chemistry 37 (24) p. 3967 (1972).
Grigg, R, et al; The Synthesis of Fused Ring Introgen Heterocycles VIA Regiospecific Intramolecular Heck Reactions Tetrahedron 46 (11) p. 4003 (1990).
Larlock, Richard C.; Comprehensive Organic Transformations VCH Publishers pp. 501-504 (1989).
Rocca, P.; First Metalation of Aryl Iodides: Directed Ortho-Lithiation of Iodopyridines, Halogen-Dance, and Application to Synthesis, J. Org. Chem., 58 p. 7832 (1993).

Affiliated with

Also associated with

Rating

Method of making asymmetric DE ring intermediates for the synthe does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method of making asymmetric DE ring intermediates for the synthe, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of making asymmetric DE ring intermediates for the synthe will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1414207