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- W2012603049 abstract "t-Butyl hydroxy-(2-iodomethyl-4-oxoazetidin-1-yl)acetate (10a), as a 1 : 1 mixture of diastereoisomers, was transformed, by sequential reactions involving thionyl chloride–2,6-lutidine and hydrogen sulphide–triethylamine, into a 1 : 1.7 mixture of t-butyl isopenam-3-exo-carboxylate (3b) and its endo-diasterepisomer (12a). Using a similar reaction sequence, p-nitrobenzyl hydroxy-(2-iodomethyl-4-oxoazetidin-1-yl)acetate (10b), as a 1 : 1 mixture of diastereoisomers, was converted into a 1 : 1.5 mixture of p-nitrobenzyl isopenam-3-exo-carboxylate (3d) and its endo-diastereoisomer (12b). In the presence of 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), the endo-compounds (12a) and (12b) underwent epimerisations to the exo-isomers (3b) and (3d)." @default.
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- W2012603049 date "1984-01-01" @default.
- W2012603049 modified "2023-10-16" @default.
- W2012603049 title "Total synthesis of analogues of the β-lactam antibiotics. Part 2. Isopenam-3-carboxylates and their 2,2-dioxides" @default.
- W2012603049 doi "https://doi.org/10.1039/p19840002785" @default.
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