Process for preparing 6- and 2-substituted-1-carbadethiapen-2-em

Details Process for preparing 6- and 2-substituted-1-carbadethiapen-2-em Process for preparing 6- and 2-substituted-1-carbadethiapen-2-em

1978-04-21

1980-05-20

Lee, Mary C.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

26032622, 424274, 560 16, C07D48704

Patent

active

042039029

ABSTRACT:
A process is disclosed for preparing antibiotic 6- and 2-substituted-1-carbadethiapen-2-em-3-carboxylic acids and their pharmaceutically acceptable salts and esters (I) ##STR1## wherein: R.sup.1 and R.sup.2 are selected from hydrogen, alkyl aryl, and aralkyl; and R.sup.3 is hydrogen, --R, --OR, or --SR, wherein R is hydrogen, alkyl, aryl or aralkyl. The process comprises complexing an appropriately substituted .delta.,.omega.-unsaturated amino acid with a transition metal carbonyl complex, followed by oxidatively induced ligand transfer and ring closure: ##STR2## wherein: F.sub.p =.eta..sup.5 --C.sub.5 H.sub.5 Fe(CO).sub.2 and F.sub.p (isobutene.sup..sym. represents a cationic complex between F.sub.p and an olefin such as isobutene, which complex cation is employed in the initial ligand exchange reaction; R.sup.4 is lower alkyl or phenyl; R.sup.5 is a readily removable blocking group or pharmaceutically acceptable ester radical; and R.sup.1, R.sup.2 and R.sup.3 are as defined above.

REFERENCES:
patent: 3950357 (1976-04-01), Kahan et al.
patent: 4013648 (1977-03-01), Horning et al.
Wong et al.; J.A.C.S. vol. 99, pp. 2823-2824 (1977).
Fieser et al., Advanced Organic Chemistry, p. 313 (1961).

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