A novel stereospecific synthesis of (±)-leukotriene A4(LTA4), methyl ester

✍ Scribed by Judith C. Buck; Frank Ellis; Peter C. North

• Publisher: Elsevier Science
• Year: 1982
• Tongue: French
• Weight: 142 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)88375-6

✦ Synopsis

The reaction of the phosphonate 1 with the epoxyaldehyde 1 1s reported as the key step In a novel stereospeclfic synthesis of (+)-LTA4, methyl ester 1

The possible implication of the leukotrienes LTC4, D4 and E4 In Immediate hypersensitivity reactlons such as allergic asthma, has prompted much interest In the synthesis of these mediators I-4 The key Intermediate leukotrlene A4 (LTA4), methyl ester serves as a common precursor to LTC4, D4 and E4 via its coupling with the appropriate thlol followed by base hydrolysis 4 This paper describes a new synthesis of (i)-LTA4, methyl ester 2 via the stereospeclflc coupling of the phosphonate 1 with the epoxyaldehyde 2 5 Clearly, the synthesis may also be applied to the preparation of