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note
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3 containing 10% of NaCl was added and the product extracted with dichloromethane. The crude product was chromatographed on silica gel eluting with n-hexane/ethyl acetate 2:1. The desired compound 5 was obtained in 17% yield together with about 40% of the unreacted pyrrolinone derived from the hydrolysis of the corresponding starting triflate.
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40
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84889104515
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note
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O-Methylation (tetramethylnaphthalendiamine/trimethyloxonium tetrafluoroborate); oxidation of methyl to carboxy (lead tetraacetate/acetic acid, silver nitrate); amidation (oxalyl chloride, ethylamine); hydrolysis and thermal decarboxylation (220 °C) of the 2-carboethoxy group.
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41
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0018173172
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Structure and absolute configuration of thienamycin
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