The synthesis of 3-(1′-hydroxyethyl)-2-azetidinone-4-yl acetic acid via dianion chemistry - an important intermediate in thienamycin total synthesis

✍ Scribed by I Shinkai; T Liu; R.A Reamer; M Sletzinger

• Publisher: Elsevier Science
• Year: 1982
• Tongue: French
• Weight: 287 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)85742-1

✦ Synopsis

A convenient synthesis of 3-cl'-hydroxyethyl)-2-azetldlnone-4-yl acetic acid, one of the key IntermedIates I" the thlenamycin total synthesis, based on the chemistry of the dlanlon derived from readily avallable Z-azetidlnone-4-yl acetic acid 1s described Recently, a practical synthesis of (?)-thienamycln (a starting from dlethyl 1,3-acetonedlcarboxylate was reported' This synthesis Involves R,S,R'-3-cl'-hydroxyethyl)-2-azetldlnone-4yl acetlc acid (k) as a key Intermediate3 In this report, we wish to describe a convenient synthesis of 3-(l'-hydroxyethyl)-2-azetldlnone-4-yl acetic acid (2 from the dlanlon derived