Preparation of substituted isoserine esters using .beta.-lactams

Details Preparation of substituted isoserine esters using .beta.-lactams Preparation of substituted isoserine esters using .beta.-lactams

1993-03-22

1995-07-04

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549511, C07D30514

Patent

active

054301602

ABSTRACT:
A process for preparing N-acyl, N-sulfonyl and N-phosphoryl substituted isoserine esters in which a metal or an ammonium alkoxide is reacted with a .beta.-lactam.

REFERENCES:
patent: 4814470 (1989-03-01), Colin 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: 4942184 (1990-07-01), Haugwitz et al.
patent: 4960790 (1990-10-01), Stella et al.
patent: 5015744 (1991-05-01), Holton
patent: 5059699 (1991-10-01), Kingston et al.
patent: 5136060 (1992-08-01), Holton
patent: 5175315 (1992-12-01), Holton
CA108: 37298c, 1988; pp. 581-582.
Witherup et al., "High Performance Liquid Chromatographic Separation of Taxol and Related Compounds From Taxus Brevifolia", Journal of Liquid Chromatography, 12(11), pp. 2117-2132 (1989).
Denis et al., "A Highly Efficient, Practical Approach to Natural Taxol", J. Am. Chem. Soc. 1988, 110, 5917-5919.
Holton "Synthesis of the Taxane Ring System", J. Am. Chem. Soc., 1984, 106 pp. 5731-5732.
Wani et al., "Plant Antitumor Agents. VI. The Isolation and Structure of Taxol, a Novel Antileukemic and Antitumor Agent from Taxus Brevifolia", J. Am. Chem. Soc., May 5, 1971, 93:9, pp. 2325-2327.
Bartholomew et al. "A New Rearrangement Reaction Conversion of 3-(chloromethyl)azetidin-2-ones to Azetidine-3-carboxylic Acid Esters", Tetrahedron Letters, vol. 32, No. 36, pp. 4795-4798, 1991.
Schulz et al., "Synthesis of New N-Radicals of Tetrazan-1-yl" Chem. Abstr., vol. 108, No. 37298c, pp. 581, 1988.
Kaiser et al., "Synthesis of Esters of Acid-Unstable Alcohols by Means of n-Butyllithium", J. Org. Chem., 1970, 35, 1198.
Mukerjee "B-Lactams: Retrospect and Prospect" Tetrahedron vol. 34, No. 52, pp. 1731-1767 (1978).
Holton et al., "A Synthesis of Taxusin" J. Am. Chem. Soc., 1988, vol. 110, No. 19, pp. 6558-6560.
Samaranayake et al., "Modified Taxols. 5. Reactions of Taxol With Electrophilic Reagents and Preparation of a Rearranged Taxol Derivative with Tubulin Assembly Activity", J. Org. Chem. 1991, vol. 56, No. 17, pp. 5114-5119.
Farina et al., "The Chemistry of Taxanes: Unexpected Rearrangement of Baccatin III During Chemoselective Debenzoylation with Bu3SnOMe/LiCl", Tetrahedron Letters, vol. 33, No. 28, pp. 3979-3982 (1992).
Deutsch et al., "Synthesis of Congeners and Prodrugs. 3. Water-Soluble Prodrugs of Taxol With Potent Antitumor Activity", J. Med. Chem., 1989, vol. 32, No. 4, pp. 788-792.
Magri et al., "Modified Taxols, 4. Synthesys and Biological Activity of taxols Modified in the Side Chain", vol. 51, No. 2, pp. 298-306 (1988).
Senilh et al., "Hemisynthese de nouveaux analoguesdu taxol. Etude de leur interaction avec la tubuline", C.R. Acad. Sc. Paris, Serie II, vol. 299, No. 15, pp. 1039-1043, Nov. 1984.
Ojima et al., "New and Efficient Approaches to the Semi-synthesis of Taxol and its C-13 Side Chain Analogs by Means of B-Lactam Synthon Method", Tetrahedron vol. 48, No. 34, pp. 6985-7012, 1992.
Chen et al., "Taxol Structure-Activity Relationships: Synthesis and Biological Evaluation of 2-Deoxytaxol", Tetrahedron Letters, vol. 34, No. 20, pp. 3205-3206 (1993).
Miller et al., "Antileukemic Alkaloids from Taxus Wallichiana Zucc", J. Org. Chem. vol. 46, No. 7, pp. 1469-1474 (1981).
Klein "Synthesis of 9-Dihydrotaxol: A Novel Bioactive Taxane" Tetrahedron Letters, vol. 34, No. 13, pp. 2047-2050 (1993).

Affiliated with

Also associated with

Rating

Preparation of substituted isoserine esters using .beta.-lactams does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Preparation of substituted isoserine esters using .beta.-lactams, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Preparation of substituted isoserine esters using .beta.-lactams will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-761281