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Novel approach for the conversion of natural Δ 3 cephalosporin derivatives into corresponding Δ 2 cephalosporin derivatives
Author(s) -
Rao Korrapati. V. V. Prasada,
Dandala Ramesh,
Handa Vija Y. K.,
Kamat Anand. G.,
Rao Inti. V. Subramanyeswara,
Rani Ananta,
Naidu Andra
Publication year - 2007
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570440643
Subject(s) - cephalosporin , chemistry , silylation , cephem , cephalosporin antibiotic , acetamide , isomerization , triethylamine , trimethylsilyl , epimer , organic chemistry , medicinal chemistry , antibiotics , carboxylic acid , catalysis , biochemistry
A simple one pot synthetic method for the isomerization of cephem double bond from the natural 3‐position to 2‐cephem positions is affected by silylation. Thus cephalosporin acids are treated with Ntrimethylsilylacetamide (MSA) or N,O ‐bis(trimethylsilyl)acetamide (BSA) and the resulting silyl esters are treated with triethylamine at ambient temperature in the same pot to afford Δ 2 ‐cephalosporins, which are potentially related compounds in cephalosporin antibacterial compounds.