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Total synthesis of dl-asparenomycins A, B and C, novel carbapenem antibiotics

✍ Scribed by Hisao Ona; Shoichiro Uyeo

Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 241 KB
Volume: 25
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)80220-3

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✦ Synopsis

Total synthesis of dl-asparenomycins was accomplished with direct conversion of carbonates 13a, 13b and l&, 14b to asparenomycin esters 15 and 16 and carboxy deprotectionby the A1C13-anisole method.

--Asparenomycin A A, a broad spectrum antibiotic with potent B-lactamase inhibitory activity, which was recently isolated from Streptomyces tokunonensis sp. nov. at our laboratories, has been shown to have a carbapenem structure with a hitherto unknown l-(hydroxymethyl)ethylidene sidechain at C6. 1 Three related antibiotics, asparenomycins B 2, C 3l and 6643-X s2 also were isolated.

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