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1.
Total syntheses of (+/-)-1-carbacefoxitin and -cefamandole and (+/-)-1-oxacefamandole.
Firestone, R A; Fahey, J L; Maciejewicz, N S; Patel, G S; Christensen, B G.
J Med Chem ; 20(4): 551-6, 1977 Apr.
Article in English | MEDLINE | ID: mdl-850241

ABSTRACT

The total syntheses of the (+/-)-1-carba analogues of cefoxitin (11), 7 alpha-methoxydeacetylcephalothin (5) and cefamandole (31) and the (+/-)-1-oxa analogue of cefamandole (43) are described. Their bioactivity spectra against 14 typical organisms are similar to those of their natural 1-thia counterparts, with the 1-carba compounds somewhat less active and the 1-oxa compound more active than the natural ones.


Subject(s)
Cefoxitin/chemical synthesis , Cephalosporins/chemical synthesis , Bacteria/drug effects , Cefamandole/analogs & derivatives , Cefoxitin/analogs & derivatives , Cefoxitin/pharmacology , Cephalosporins/pharmacology , Methods , Microbial Sensitivity Tests
2.
Total synthesis of beta-lactam antibiotics. VI. 3-Arylcephalosporins.
Firestone, R A; Maciejewicz, N S; Christensen, B G.
J Org Chem ; 39(23): 3384-7, 1974 Nov 14.
Article in English | MEDLINE | ID: mdl-4427185

Subject(s)
Cephalosporins/chemical synthesis , Benzene Derivatives/chemical synthesis , Methods , Thiazoles/chemical synthesis
3.
Total synthesis of beta-lactam antibiotics. IV. Epimerization of 6(7)-aminopenicillins and -cephalosporins from alpha to beta.
Firestone, R A; Maciejewicz, N S; Ratcliffe, R W; Christensen, B G.
J Org Chem ; 39(4): 437-40, 1974 Feb 22.
Article in English | MEDLINE | ID: mdl-4814781

Subject(s)
Cephalosporins/chemical synthesis , Penicillins/chemical synthesis , beta-Lactams , Benzaldehydes , Chemical Phenomena , Chemistry , Hydrogen-Ion Concentration , Kinetics , Lithium , Methods , Protons
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