Stereocontrolled acetoxyazetidinone process

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

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540357, C07D49900, A61K 31425

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active

046393358

ABSTRACT:
A novel stereocontrolled process is disclosed for converting 6-aminopenicillanic acid to an optically active azetidinone of the formula ##STR1## wherein R" is a hydroxy-protecting group by use of a 6,6-dihaloanhydropenicillin or 6,6-bis(phenylselenyl)anhydropenicillin intermediate.

REFERENCES:
patent: 4468351 (1984-08-01), Pirie et al.
Heterocycles 17: 201-207 (1982) Hirai et al., J. Org. Chem. 42: 2960-2965 (1977) DiNinno et al.
Tetrahedron Letters 23(39): 4021-4024 (1982) Hirai et al.
Tetrahedron Letters 23(22): 2293-2296 (1982) Reider et al.
Chem. Pharm. Bull 29(11): 3158-3172 (1981) Hayashi et al.

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