94292-84-9Relevant academic research and scientific papers
SYNTHESIS OF 5S-HYDROXY-14,15 LTA4 A BIOGENIC PRECURSOR TO THE LIPOXINS
Leblanc, Yves,Fitzsimmons, Brian J.,Rokach, Joshua
, p. 3449 - 3452 (2007/10/02)
A synthesis of 5S-hydroxy-14,15-LTA4 10 an intermediate in the biosynthesis of the lipoxins is described.
Stereocontrolled Total Synthesis of Lipoxins A
Nicolau, K. C.,Veale, C. A.,Webber, S. E.,Katerinopoulos, H.
, p. 7515 - 7518 (2007/10/02)
A stereocontrolled total synthesis of lipoxin A and a number of its isomers is reported.The strategy involves Sharpless asymmetric epoxidation and pinylborane asymmetric reduction to build the hydroxy-bearing stereocenters and a Wittig-type as well as a P
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 (2007/10/02)
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.
SYNTHESIS OF LIPOXINS: TOTAL SYNTHESIS OF CONJUGATED TRIHYDROXY EICOSATETRAENOIC ACIDS
Adams, Julian,Fitzsimmons, Brian. J.,Rokach, Joshua
, p. 4713 - 4716 (2007/10/02)
The first synthesis of a conjugated trihydroxy eicosatetraenoic acid, a possible structure for Lipoxin A is described.A biomimetic approach was utilized.
