Methods and compounds for the preparation of carbacephems

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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540364, C07D47104, C07D41304, C07B 4304

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active

055213073

ABSTRACT:
A chiral process for preparing compounds of the formula: ##STR1## from a compound of the formula: ##STR2## in which the compound formula (IV) is reacted with trimethylsilyl iodide to remove the chiral auxiliary at the 7-position and the carboxy protecting group. The process allows for the retention of the amino and carboxy protecting groups throughout the preparation of Compound IV. Also disclosed are novel intermediates.

REFERENCES:
patent: 4665171 (1987-05-01), Evans et al.
Spitzer, J. Org Chem 39, 2468 (1974).
Caputo, Tet. Letters 1967, p. 4729.
Klein, Tet. Letters 1975, 4249.
Piatak, J. Org. Chem. 34, 116(1969).
Deno, Tet. Letters 1977, 1703.
Wolfe, Chem Comm 1970, 1420.
Liotta, J. Org Chem 45, 2887 (1980).
Ayers Chem Comm 1972, 428.
Jackson, et al., Synthesis of Carbacephem Antibiotics: Synthesis via Dieckmann Reaction Using Phenylesters to Direct the Regioselectivity of the Cyclization, 31 Tet. Letters 6317 (1990).

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