Process for production of ceophalosporins

Details Process for production of ceophalosporins Process for production of ceophalosporins

1988-03-23

1989-08-08

Rizzo, Nicholas S.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540215, 540222, C07D50104, C07D47104

Patent

active

048554189

ABSTRACT:
Cephalosporin and 1-carba(1-dethia)cephalosporin antibiotics substituted in the 3-position with, inter alia, alkyl, alkenyl and alkynyl, are provided via process comprising conversion of a cephalosporin or 1-carba(1-dethia)-3-cephem substituted in the 3-position with halogen or a sulfonyloxy ester with Pd(O) mediated alkylation with organostannanes.

REFERENCES:
patent: 4673737 (1987-06-01), Evans et al.
Chemical Abstracts, vol. 87;135362m, (1987).
W. J. Scott, et al., "Palladium-Catalyzed Coupling of Vinyl Triflates with Organostannanes. A Short Synthetis of Pleraplysillin-I", J. Am. Chem. Soc., 1984, 106, 4630-4632.
J. K. Stille, "The Palladium-Catalyzed Cross-Coupling Reactions of Organotin Reagents with Organic Electrophiles", Angew. Chem. Int. Ed. Engl., 25, (1986), 508-524.
M. R. Pena and J. K. Stille, "Attachment of the Anthramycin Acrylamide Side Chain by the Palladium Catalyzed Coupling Reaction of a Vinyl Triflate", Tetrahedron Letters, vol. 28, No. 52, pp. 6573-6576, 1987.
F. Orsini and F. Pelizzoni, "Pd(O)-Mediated Cross-Coupling of Reformatsky Reagents with Vinyl- and Aryl Triflates", Synthetic Comm., 17(12), 1389-1402, (1987).
A. M. Echavarren and J. K. Stille, "Palladium-Catalyzed Coupling of Aryl Triflates with Organostannes", J. Am. Chem. Soc., 1987, 109, 5478-5486.
H. M. Colquhoun, "Homogenous, Palladium-Catalysed, Carbon-Carbon Bond Formation", Chemistry and Industry, Sep. 7, 1987, pp. 612-617.
E. Negishi et al., "Palladium- or Nickel-Catalyzed Reactions of Alkenylmetals with Unsaturated Organic Halides as a Selective Route to Arylated Alkenes and Conjugated Dienes: Scope, Limitations and Mechanism", J. Am. Chem. Soc., 1987, 109, 2393-2401.
J. K. Stille and J. H. Simpson, "Stereospecific Palladium-Catalyzed Coupling Reactions of Vinyl Iodides with Acetylenic Tin Reagents", J. Am. Chem. Soc., 1987, 109, 2138-2152.
T. N. Mitchell, "Transition-Metal Catalysts in Organotin Chemistry", J. of Organometallic Chemistry, 304, (1986), 1-16.
L. Castedo et al., "Palladium-Catalyzed Synthesis of Dienynes Related to Vitamin D from Enol Triflates", Tetrahedron Letters, vol. 27, No. 13, pp. 1523-1526.
J. K. Stille, "Palladium Catalyzed Coupling of Organotin Reagents with Organic Electrophiles", Pure & Appl. Chem., vol. 57, No. 12, pp. 1771-1780, 1985.
W. J. Scott et al., "Palladium-Catalyzed Olefination of Vinyl Triflates", J. Org. Chem., 1985, 50, 2302-2308.
W. J. Scott and J. K. Stille, "Palladium-Catalyzed Coupling of Vinyl Triflates with Organostannanes. Synthetic and Methanistic Studies", J. Am. Chem. Soc., 1986, 108, 3033-3040.
L. A. Paquette et al., "Total Synthesis of (.+-.)-Sterpuric Acid", Tetrahedron Letters, vol. 28, No. 92, pp. 5017-5020, 1987.

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