Short synthetic route to taxol and taxol derivatives

Details Short synthetic route to taxol and taxol derivatives Short synthetic route to taxol and taxol derivatives

1994-05-24

1996-04-16

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549214, C07D31306

Patent

active

055084478

ABSTRACT:
A short route to the total synthesis of the core skeleton of the taxol ring system is described. The same sequence of transformations can be carried out to make the 7-hydroxy series, and connect the additional carbon atoms required for the A-ring. The number of steps to the taxane skeleton is 13, making it the shortest route from readily available inexpensive starting materials.

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: 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: 5157049 (1992-10-01), Haugwitz et al.
patent: 5175315 (1992-12-01), Holton
patent: 5194635 (1993-03-01), Kingston et al.
patent: 5200534 (1993-04-01), Rao
patent: 5296506 (1994-03-01), Kingston et al.
patent: 5405972 (1994-01-01), Holton et al.
patent: 5461169 (1995-10-01), Nicolaou et al.
March, J., "Advanced Organic Chemistry", 2nd ed., pp. 246-248, 1977.
Stu Borman, "Scientists Mobilize to Increase Supply of Anticancer Drug Taxol," C&EN, pp. 11-18, Sep. 1991.
Brieva et al., "Chemoenzymatic Synthesis of the C-13 Side Chain of Taxol; Optically-Active 3-Hydroxy-4-phenyl .beta.-Lactam Derivatives," J. Org. Chem., 58:1068-1075, 1993.
Marilyn Chase, "A New Cancer Drug May Extend Lives--At Cost of Rare Trees," The Wall Street Journal, Apr. 9, 1991.
Chen et al., "Taxol Structure-Activity Relationships: Synthesis and Biological Evaluation of 10-Deoxytaxol," The Journal of Organic Chemistry, 58(11):2927-2928, 1993.
Chen., "Taxol Structure-Activity Relationships: Synthesis and Biological Evaluation of 2-Deoxytaxol," Tetrahedron Letters, 34(20):pp. 3205-3206, 1993.
Faye Flam, "Race to Synthesize Taxol Ends in a Tie," Science, vol. 263:p. 911, 1994.
Georg et al., "Asymmetric Synthesis of .beta.-Lactams and N-Benzoyl-e-Phenylisoserines Via the Staudinger Reaction, " Tetrahedron Letters, 32(27):pp. 3151-3154, 1991.
Georg et al., "Galactose-Imines in the Staudinger Reaction," Tetrahedron Letters, 33(16):pp. 2111-2114, 1992.
Golinski et al., "An Enantioselective Approach to Ring of Taxol Using The Wieland-Miescher Ketone,"0 Tetrahedron Letters, 34(1):pp. 55-58, 1993.
Gou et al., "A Practical Chemoenzymatic Synthesis of the Taxol C-13 Side Chain N-Benzoyl-(2R,3S)-3-phenylisoserine," J. Org. Chem., 58:pp. 1287-1289, 1993.
Holton et al., "First Total Synthesis of Taxol. 1. Functionalization of the B Ring," J. Am. Chem. Soc., 116:pp. 1597-1598, 1994.
Jones et al., "An Asymmetric Synthesis of MK-0417. Observations on Oxazaborolidine-Catalyzed Reductions," J. Org. Chem., 56-pp. 763-769, 1991.
Larry L. Klein, "Synthesis of 9-Dihydrotaxol: A Novel Bioactive Taxane," Tetrahedron Letters, 34(13):pp. 2047-2050, 1993.
Jubert and Knoche, "Preparation of New Classes of Aliphatic, Allylic, and Benzylic Zinc and Copper Reagents by the Insertion of Zinc Dust into Organic Halides, Phosphates, and Sulfonates," J. Org. Chem., 57:pp. 5425-5431, 1992.
Magee et al., "A straightforward Route to Functionalized Intermediates Containing the CD of Taxol," J. Org. Chem., 57(12):pp. 3274-3276, 1992.
Wender and Mucciaro, "A New and Practical Approach to the Synthesis of Taxol and Taxol Analogues: The Pinene Path," J. Am. Chem. Soc., 114:pp. 5878-5879, 1992.
Nicolaou et al., "A Convergent Strategy Towards Taxol. A Facile Enantioselective Entry Into a Fully Functionalized Ring a System," J. Chem. Soc., Chem. Commun., pp. 1117-1118, 1992.
Nicolaou et al., "Total Synthesis of Taxol," Nature, 367:pp. 630-634, 1994.
Nicolaou et al., "Novel Chemistry of Taxol. Retrosynthetic and Synthetic Studies," J. Chem. Soc., Chem. Commun., pp. 295-296, 1994.
Nicolaou et al., "Synthesis of Novel Taxoids," J. Am. Chem. Soc., 116:pp. 1591-1592, 1994.
Ojima et al., "New and Efficient Approaches to the Semisynthesis of Taxol and Its C-13 Side Chain Analogs by Means of .beta.-Lactam Synthon Method," Tetrahedron, 48(34):pp. 6985-7012, 1992.
Wender and Rawlins, "Toward the Synthesis of the Taxol C,D. Ring System: Photolysis of .alpha.-Methoxy Ketones," Tetrahedron, 48(34):pp. 7033-7048, 1992.
Winkler and Subrahmanyam, "Studies Directed Towards the Synthesis of Taxol: Preparation of C-13 Oxygenated Taxane Congeners," Tetrahedron, 48(34):pp. 7049-7056, 1992.
Charles S. Swindell, "Taxane Diterpene Synthesis Strategies. A Review," Organic Preparations and Procedures Int., pp. 465-543, 23(4), 1991.
Ojima et al., "Synthesis and Structure--Activity Relationships of Novel Nor-Seco Analogs of Taxol and Taxotere," J. Org. Chem., 59:pp. 515-517, 1994.
Wang et al., "A Straightforward Approach to the Synthesis of the Tricyclic Core of Taxol," J. Org. Chem., 58:pp. 2931-2932, 1993.
Emmer and Weber-Roth, "Synthesis of Derivatives of FK 506 and FR 900520: Modifications at the Binding Domain," Tetrahedron, 48(28):pp. 5861-5874, 1992.
Borman, Stu, "Higher Yield Synthetic Route To Cyclic Enediynes Developed," Chemical & Engineering, Aug. 28, 1995:28-30.
Thayer, Ann, "Firms Dispute Cancer Drug Patent Rights," Chemical & Engineering, Oct. 30, 1995:8.
International Search Report, Sep. 29, 1995.

Affiliated with

Also associated with

Rating

Short synthetic route to taxol and taxol derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Short synthetic route to taxol and taxol derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Short synthetic route to taxol and taxol derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-326437