3-Unsaturated alkyl cephems from 3-triflyl cephems

Details 3-Unsaturated alkyl cephems from 3-triflyl cephems 3-Unsaturated alkyl cephems from 3-triflyl cephems

1987-02-26

1989-09-26

Daus, Donald G.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540219, 540225, 556 86, C07D50120

Patent

active

048701688

ABSTRACT:
There is disclosed a process for the production of certain 3-hydrocarbyl-3-cephem derivatives wherein the hydrocarbyl group is selected from 1-alkenyl and conjugated and unconjugated 1-polyalkenyl, 1-alkynl, carbocyclic and heterocyclic aryl, and carbocyclic and heterocyclic arylmethyl and, in the case of the 1-alkenyl and conjugated 1-polyalkenyl derivatives, with substantially complete stereospecificity, by coupling a 3-triflyloxy cephem with a hydrocarbyltributylstannane in the presence of bis(dibenzylideneacetonyl)-palladium, a phosphine, and a metal halide such as, for example, zinc chloride. The 3-unsaturated alkyl-3-cephem derivatives so-produced are useful as broad-spectrum antibacterial agents.

REFERENCES:
patent: 3959324 (1976-05-01), Peterson
Scott (I) (1984) J. Am. Chem. Soc., v. 106, p. 4630-4632.
Scott (II) (1986) J. Am. Chem. Soc., v. 108, pp. 3033-3040.

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