- SYNTHESIS OF 5S-HYDROXY-14,15 LTA4 A BIOGENIC PRECURSOR TO THE LIPOXINS
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A synthesis of 5S-hydroxy-14,15-LTA4 10 an intermediate in the biosynthesis of the lipoxins is described.
- Leblanc, Yves,Fitzsimmons, Brian J.,Rokach, Joshua
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p. 3449 - 3452
(2007/10/02)
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- SIMPLE SYNTHESIS AND ASSIGNMENT OF STEREOCHEMISTRY OF LIPOXIN A
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A synthesis of lipoxin A, a recently descovered biologically active eicosanoid, and the assignment of stereoformula 1 is reported herein.
- Corey, E. J.,Su, Wei-gou
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p. 281 - 284
(2007/10/02)
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- Stereocontrolled Total Synthesis of Lipoxins A
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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
- Nicolau, K. C.,Veale, C. A.,Webber, S. E.,Katerinopoulos, H.
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p. 7515 - 7518
(2007/10/02)
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- Enantiospecific and Stereospecific Synthesis of Lipoxin A. Stereochemical Assignment of the Natural Lipoxin A and Its Possible Biosynthesis
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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.
- Adams, Julian,Fitzsimmons, Brian J.,Girard, Yves,Leblanc, Yves,Evans, Jillian F.,Rokach, Joshua
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p. 464 - 469
(2007/10/02)
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- SYNTHESIS OF LIPOXINS: TOTAL SYNTHESIS OF CONJUGATED TRIHYDROXY EICOSATETRAENOIC ACIDS
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The first synthesis of a conjugated trihydroxy eicosatetraenoic acid, a possible structure for Lipoxin A is described.A biomimetic approach was utilized.
- Adams, Julian,Fitzsimmons, Brian. J.,Rokach, Joshua
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p. 4713 - 4716
(2007/10/02)
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