New stereospecific syntheses and x-ray diffraction structures of (−)-D-erythro- and (+)-L-threo-4-fluoroglutamic acid

✍ Scribed by Milos Hudlicky; Joseph S. Merola

• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 282 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)88500-7

✦ Synopsis

Abrrracr . Stereospecific syntheses of (+)-L-rlrreo and (-)-D-eryrhro-4-fluoroglutamic acid am based on the hydrolysis of methyl l-acetyl-4-fluoro-L-pyrroklin-5-one-2-carboxylate, prepared from rrans-and cis-4hydmxyproliues, respectively. After the discovery of the antimetabolic properties of fluorociaic acid' and %fluorouracil,2 4fluoroglutamic acid of undefined sternochemistry was synthesized with the expectation, that, as a potential antimetabolite of glutamic acid, it might inhibit growth of bacteria and neoplastic tissues.3'7 Its derivative, fluoromethottexate, was found to possess antitumor properties. *-lo Current interest focuses on the effects of 4-