You can consider ring-opening reactions that cleave the beta-lactam ring of penicillin. This can result in a variety of functional groups depending on the reaction conditions and reagents used.
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benzyl (2S,3S,6R,7R)-3-chloroacetoxy-3-methyl-8-oxo-7-phenoxyacetamido-5-thia-1-azabicyclo<4.2.0>octane-2-carboxylate
Benzoic acid (2R,4R,5S,6S)-4-(bis-ethylsulfanyl-methyl)-6-[(R)-(tert-butyl-diphenyl-silanyloxy)-methylcarbamoyl-methyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yl ester
cis-2-hydroxy-cis-3-methylcyclohexanol
[(1R,6S)-6-(aminomethyl)cyclohex-3-en-1-yl]methanol
N-Methyl-2-(methylthio)aniline
1-methylcyclobutanol acetate
Benzenepentanoic acid, b-hydroxy-, methyl ester
7
8
9
1-(1-benzoyl-2-(4-chlorophenyl)cyclopropyl)ethanone
Iodine
(1S,2R,4S,5R,6S)-3-Oxa-tricyclo[3.2.1.02,4]octan-6-ol
2,4-adamantanedione
1-(2-(2-(but-3-enyl)-2-phenylcyclopropylidene)-1-phenylvinyl)benzene
Os3(CO)10{SC(H)C6H5C(H)C(H)C6H5}(H)
6-(Toluene-4-sulfonyl)-decan-5-ol
Benzoic acid (4aR,6S,7R,8S,8aR)-6-bromo-2-methyl-8-(toluene-4-sulfonyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
(S)-N-<3-methyl-3-(4-methyl-3-cyclohexen-1-yl)cyclobutylidene>-benzenesulfenamide
(S)-N-(2-bromo-2-phenylethyl)-4-methylbenzenesulfonamide
diethyl 2-(4-methylenehex-1-yl)malonate
{(1E,3Z)-4-[2-(4-Chloro-phenyl)-2H-tetrazol-5-yl]-buta-1,3-dienyl}-dimethyl-amine
(-)-trans-2.3-Diphenyl-cyclopropancarbonsaeure
Acetylcyclosporin 4,7-bis(benzyl thioamidate)
4-phenyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone
(E)-3-(m-tolyl)allyl acetate
(1R,2R)-2-chloro-1,2-bis(4-chlorophenyl)ethanol
1,2',6',2''-tetra-N-benzyloxycarbonyl-2-chloro-2-deoxyfortimicin A
(2S,3S)-2-amino-3-(5,5-diphenyl-4,5-dihydro-isoxazol-3-yl)-3-hydroxy-propionic acid methyl ester
methyl 5-methoxy-2-oxo-cyclohexan-1-carboxylate
Benzene, 1,1'-[3-methyl-3-(1-methyl-2-propenyl)-1-cyclopropene-1,2-diyl]bis-
cis-5-fluoro-2-phenyl-2-pentene
