Simple synthesis and assignment of stereochemistry of lipoxin A

✍ Scribed by E.J. Corey; Wei-guo Su

• Publisher: Elsevier Science
• Year: 1985
• Tongue: French
• Weight: 249 KB
• Volume: 26
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)80797-8

✦ Synopsis

A synthesis of lipoxm A, a recently discovered biologically active eicosanoid, and the assignment of stereoformula ,l_ is reported herein. Serhan, Hamberg and Samuelason have recently described the isolation of a 5,6,15s-trihydroxy-7,9,11,13-eicosatetraenoic acid from human leukocytes exposed to 15-HPETE (15S_hydroperoxy_5g, 8z, llz, 13E-eicosatetrenoic acid) in the presence of calcium ionophore A23187. ' These workers have termed this substance lipoxin A (LX-A) and have shown it to have interesting biological activity (stimulation of elastase and superoxide ion release from neutrophils, an activity shared with leukotriene B4). 2 We report herein an effective synthesis of this substance which makes it obtainable in quantity from arachidonic acid without the need for resolution. Native lipoxin A is available in submicrogram or microgram amounts only with difficulty (and biosynthesis requires access to a supply of human neutrophils). The availability of synthetic material (which has been identified by comparison with biosynthetic lipoxin A) should accelerate the study of the biological role of this new eicosanoid. The synthetic route reported herein allows the assignment of stereoformula $_ to lipoxin A.