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An improved entry to a key intermediate for thienamycin synthesis from methyl (R)-3-hydroxybutanoate via direct epimerization at C-3 on 2-azetidinone rings

✍ Scribed by Toshiyuki Chiba; Takeshi Nakai


Book ID
104228927
Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
137 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis


An improved entry to a key thienamycin intermediate is described which relies upon the direct epimerization at C-3 of the 3-(1-hydroxyethyl)-2azetidinone derivatives readily obtained from methyl (R)-3-hydroxybutanoate. Thienamycin (A) has been the focus of current synthetic attention. 2 Recently we have reported a synthetic route to the key thienamycin intermediate (2) based on the enolate-imine condensation of methyl (R)-3-hydroxybutanoate (2) with the