Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-12-05
1997-04-15
Chang, Ceila
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549 20, C07D40506
Patent
active
056211082
ABSTRACT:
Novel processes for the preparation of lactam- and lactone-containing macrocyles are provided. In preferred embodiments, rapamycin and demethoxyrapamycin are prepared by a convergent synthesis regime. Intermediates useful in the synthetic processes are also provided.
REFERENCES:
patent: 5164399 (1992-11-01), Failli et al.
patent: 5252579 (1993-10-01), Skotnicki et al.
Crisp, G. and Glink, "Elaboration of the Side Chain of .alpha.-Amino Acids Containing a Vinyl Iodide by Palladium-Catalysed Coupling", Tetrahedron 1994, 50(8), 2623-2640.
Eshelman, J. et al., "Diastereoselective [2,3] Wittig Rearrangement of Carbohydrate-derived Tertiary Allylic Ethers. 1. Synthesis of the C.sup.11 -D.sup.18 Subunit of Herbimycin A From D-Glucose", Tetrahedron Letters 1993, 34(5), 749-752.
Goulet, M.T. and Boger, "Degradative Studies on the Tricarbonyl Containing Macrolide Rapamycin", Tetrahedron Letters 1990, 31(34), 4845-4848 and Corrigendum Tetrahedron Letters 1991, 32, 6454.
Condon, S. et al., "Studies Directed Towards the Total Synthesis of Rapamycin: Construction of a C29-C39 Fragment", Thirty-Third National Organic Chemistry Symposium Program and Abstracts, Jun. 13-17, 1993, Montana State University, Bozeman, Montana.
Smith III, A. et al., "Rapamycin and Demethoxyrapamycin: Synthetic Studies", American Chemical Society, Division of Organic Chemistry, 207th ACS National Meeting, Mar. 13-17, 1994, San Diego, CA.
Smith III, A. et al, "The Total Syntheses of Rapamycin and Demethoxyrapamycin", American Chemical Society, Division of Organic Chemistry, 209th ACS National Meeting, Apr. 206, 1995, Anaheim, CA.
Teague et al. "Synthesis and study of a non macrocyclic FK506 derivative" CA 121:255492 (1994).
Batchelor, M.J. et al., "A Novel Application of the Dess-Martin Reagent to the Synthesis of an FK506 Analogue and Other Tricarbonyl Compounds", Tetrahedron 34, 167-170 (1993).
Chen, S. et al., "Application of the Ibuka-Yamamoto Reaction to a Problem in Stereochemical Communication: A Strategy for the Stereospecific Synthesis and Stabilization of the Triene Substructure of Rapamycin Through Sulfone Substitution", J. Org. Chem. 1991, 56, 5834-5845.
Corey, E.J. and Fuchs, "A Synthetic Method for Formyl-Ethynyl Conversion (RCHO-RC=CH or RC=CR.sup.1)", Tetrahedron Letters 1972, 13, 3769-3772.
Crisp, G. et al., "Synthesis and Transformation of Trialkylstannyl-Substituted Allylglicine Derivatives", Tetrahedron Letters 1992, 33(32), 4649-4652.
Dess, D.B. et al., "Readily Accessible 12-I-5.sup.1 Oxidant for the Conversion of Primary and Secondary Alcohols to Aldehydes and Ketones", J. Org. Chem. 1983, 48, 4155-4156.
Fisher, M. et al., "Synthetic Studies Toward Rapamycin: A Solution to a Problem in Chirality Merger Through Use of the Ireland Reaction", J. Org. Chem. 1991, 56, 5826-5834.
Greene, T.W. and Wuts, Protective Groups in Organic Synthesis, 2d Ed., Wiley & Sons, 1991.
Hayward, C. et al., "An Application of the Suarez Reaction to the Regiospecific and Stereospecific Synthesis of the C.sub.28 -D.sub.42 Segment of Rapamycin", Tetrahedron Letters 1993, 34(25), 3989-3992.
Hayward, C. et al., "Total Synthesis of Rapamycin vi a Novel Titanium-Mediated Aldol Macrocyclization Reaction", J. Am. Chem. Soc. 1993, 115, 9345-9346.
Horvath, R. et al., "An Applicaiton of the Evans-Prasad 1,3-Syn Diol Synthesis to a Stereospecific Synthesis of the C.sub.10 -C.sub.27 Segment of Rapamycin", Tetrahedron Letters 1993, 34(25), 3993-3996.
March, J. Advanced Organic Chemistry, Fourth Ed., Wiley & Sons, New York, 1992, p. 1194.
Meyer, S. et al., "Synthetic Investigations of Rapamycin. I. Synthesis of a C.sub.10 -C.sub.21 Fragment", J. Org. Chem. 1992, 57, 5058-5060.
Nicolaou, et al., "Stereocontrolled Total Synthesis of Lipoxins B", Synthesis 1986, 453-461.
Nicolaou, K. et al., "Total Synthesis of Rapamycin", J. Am. Chem. Soc. 1993, 115, 4419-4420.
Nicolaou, K. et al., "Stereoselective Construction of the C.sup.21 -C.sup.42 Fragment of Rapamycin", J. Chem. Soc., Chem. Commun. 1993, 619-622.
Piscopio, A.D. et al., "A Highly Convergent Strategy Towards Rapamycin. Stereoselective Construciton of the C.sup.8 -C.sup.18 Fragment", J. Chem. Soc., Chem. Commun. 1993, 617-618.
Romo, D. et al., "Synthetic Investigations of Rapamycin. 2. Synthesis of a C.sub.22 -C.sub.42 Fragment", J. Org. Chem. 1992, 57, 5060-5063.
Romo, D. et al., "Total Synthesis of (-)-Rapamycin Using an Evans-Rischchenko Fragment Coupling", J. Am. Chem. Soc. 1993, 115, 7906-7907.
Smith, A.B. et al., "Rapamycin Synthetic Studies. 1. Construction of the C(27)-C(24) Subunit", Tetrahedron Letters 1994, 35(28), 4907-4910.
Smith, A.B. et al., "Rapamycin Synthetic Studies. 2. Elaboration of the C(10)-C(26) Perimeter", Tetrahedron Letters 1994, 35(28), 4911-4914.
Yohannes, D. and Danishefsky, "Degradation of Rapamycin: Retrieval of Major Intact Subunits", Tetrahedron Letters 1992, 33(49), 7469-7472.
Yohannes, D. et al., "Degradation of Rapamycin: Synthesis of a Rapamycin Derived Fragment Contianing the Tricarbonyl and Triene Sectors", Tetrahedron Letters 1993, 34(13), 2075-2078.
Zhang, H. et al., "Palladium- and Molybdenum-Catalyzed Hydrostannation of Alkynes. A Novel Access to Regio- and Stereodefined Vinylstannanes", J. Org. Chem. 1990, 55, 1857-1867.
Anderson, J.C. et al., "Studies towards the total synthesis of rapamycin: a convergent and stereoselective synthesis of the C.sub.22 -C.sub.32 carbon framework", Tetrahedron Letters 1994, 35(13), 2087-2090.
Crisp, G.T. and Glink, P.T., "Elaboration of the side chain of .alpha.-Amino acids by palladium-catalysed stille couplings", Tetrahedron Letters 1994, 50(10), 3213-3234.
Boden, E. and Keck, "Proton-Transfer Steps in Steglich Esterification: A Very Practical new Method for Macrolactonization", J. Org. Chem. 1985, 50, 2394-2395.
Farina, V. and Krishman, B., "Large rate accelerations in the stille reaction with tri-2-furylphosphine and triphenylarsine as palladium ligands: mechanistic and synthetic implications", J. Am. Chem. Soc. 1991, 113, 9585-9595.
F er ezou, J.P. et al., "Model studies of palladium-catalysed coupling reactions for the South-North attachment of avermectins", Synlett 1991, Jan., 53-56.
Hale, M.R., and Hoveyda, A.H., "Siloxanes: Versatile templates for acyclic stereocontrol. Synthesis of the C27-C33 segment of rapamycin", J. Org. Chem. 1992, 57, 1643-1645.
Kalivretenos, A. et al., "Synthesis of .beta.-resorcyclic macrolides via organopalladium chemistry. Application to the total synthesis of (S)-searalenone", J. Org. Chem. 1991, 56, 2883-2894.
Kouklovsky, C. et al., "Studies towards the total synthesis of rapamycin: preparation of the cyclohexyl C.sub.33 -C.sub.42 fragment and further coupling to afford the C.sub.22 -C.sub.42 carbon unit", Tetrahedron Letters 1994, 35(13), 2091-2094.
Ley, S.V. et al., "Studies towards the total synthesis of rapamycin: preparation of the C.sub.10 -C.sub.17 carbon unit", Tetrahedron Letters 1994, 35(13), 2095-2098.
Mc Murry, J.E. and Scott, W.J., "A method for the regiospecific of enol triflates by enolate trapping", Tetrahedron Letters 1983, 24(10), 979-982.
Mc Murry, J.E. and Scott, W.J., "A new method of olefin synthesis. coupling of lithium dialkulcuprates with enol triflates", Tetrahedron Letters 1980, 21, 4313-4316.
Reich, H.J. et al., "Solution Ion pair structure of 2-lithio-1,3-dithianes in THF and THF-HMPA", Tetrahedron Letters 1994, 50(20), 5869-5880.
Sin, N. and Kallmerten, "Diastereoselective [2,3] wittig rearrangement of carbohydrate-derived tertiary allylic ethers. 2. Synthesis of an advanced rapamycin intermediate from d-glucose", Tetrahedron Letters 1993, 34(5), 753-756.
Stille, J.K. and Tanaka, M., "Intramolecular palladium-catalyzed cyclizations of esters containing vinyl triflate and vinylstannane groups at the termini: synthesis of large-ring lactones", J. Am. Chem. Soc. 1987, 109, 3785-3786.
Stille, J.K. and Groh, B.L., "Stereospecific cross-coupling of vinyl halides with vinyl tin reagents catalyzed by palladium", J. Am. Chem. Soc. 1987, 109, 813-817.
Zibuck, R. et al., "Total synthesis of (+)-latrunculin B", J. Am. Chem. Soc. 1986, 108, 2451-2453.
B
Condon Stephen M.
Leahy James W.
Leazer, Jr. Johnnie L.
Maleczka Robert E.
McCauley John A.
Chang Ceila
Trustees of the University of Pennsylvania
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