Stereospecific synthesis of thienamycin from penicillin

Details Stereospecific synthesis of thienamycin from penicillin Stereospecific synthesis of thienamycin from penicillin

1982-06-22

1984-04-24

Berch, Mark L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602452R, 260141, 556418, C07D20508, C07D48704, C07F 704

Patent

active

044446853

ABSTRACT:
A stereospecific conversion of penicillin to thienamycin, using diisopropylamine borane and magnesium trifluoroacetate to prepare the hydroxyethyl side chain and acetoacetate dianion equivalent disilylethyl to prepare the .beta.-ketoester side chain.

REFERENCES:
Brownbridge et al., Synthesis 1983, pp. 85-104.
Chan et al., J. Amer. Chem. Soc. 102, 3534 (1980).
Andrews et al., Tet. Letters 21, 693 (1980).
Andrews et al., Tetrahedron 21, 697 (1980).
Noth et al., Chem. Berichte 93, 1078 (1960).
Mellilo et al., Tet. Letters 21, 2783 (1980).

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