94235-45-7Relevant academic research and scientific papers
Enantiospecific and Stereospecific Synthesis of Lipoxin A. Stereochemical Assignment of the Natural Lipoxin A and Its Possible Biosynthesis
Adams, Julian,Fitzsimmons, Brian J.,Girard, Yves,Leblanc, Yves,Evans, Jillian F.,Rokach, Joshua
, p. 464 - 469 (1985)
Both chemical and enzymatic steps were employed to convert leukotriene A4 and its unnatural epoxide isomers into four diastereomeric 5(S),6(S),15(S)-trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acids, possible structures for lipoxin A.These compounds were correlated with trihydroxy tetraene eicosatetraenoic acids derived from tetraene epoxide 3, and the relative stereochemistries of the 5 and 6 positions were assigned.These assignments were confirmed by total synthesis of two diastereomers of lipoxin A.One of these isomers, 5(S),6(S),15(S)-trihydroxy-7-9,13-trans-11-cis-eicosatetraenoic acid (1b), corresponded to lipoxin A derived from natural sources.The structure and possible biosyntheses of lipoxin A are proposed.
