An efficient synthesis of leukotriene B4

Avignon-Tropis, M.; Treilhou, Michel; Lebreton, Jacques; Pougny, Jean-René; Fréchard-Ortuno, I.; Huynh, Chanh; Linstrumelle, G.

doi:10.1016/s0040-4039(01)93886-9

Cited by 13 publications

(4 citation statements)

References 6 publications

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“…Various organometallic cross-coupling reactions (Miyaura-Suzuki, [10][11][12] Sonogashira [13][14][15][16] ), stereoselective olefination reactions (Horner-Wadsworth-Emmons [17][18][19][20] or Wittig reactions [21][22][23] ), intramolecular [24] or radical [25] rearrangements, addition of Z-vinylbromide to aldehyde, and also addition of vinyl lithium reagents to pyrilium tetrafluoroborates [26] have been successfully reported to build the conjugated triene. These interesting papers document the difficulty in the syntheses of PUFA metabolites containing a conjugated triene and thus, some previously retrosynthetic approaches may be borrowed to achieve the synthesis of dihydroxylated docosatrienes.…”

Section: Introductionmentioning

confidence: 99%

A Versatile and Stereocontrolled Total Synthesis of Dihydroxylated Docosatrienes Containing a Conjugated E,E,Z‐Triene

Dayaker¹,

Balas²

2014

Chemistry A European J

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A versatile strategy featuring a Colvin rearrangement, hydrozirconation, a Sonogashira cross-coupling reaction and a Z-selective Wittig olefination, was successfully developed for the construction of a conjugated E,E,Z-triene subunit, flanked on both sides by two Z-allylic hydroxyl groups. This chemical pattern is found in many endogenous lipid metabolites such as maresin 1 (MaR1), neuroprotectin D1 (NPD1), and its aspirin triggered-isomer AT-NPD1, which not only counter-regulate inflammation but also actively orchestrate (at nanomolar doses) the resolution and termination program of acute inflammation while promoting wound healing, return to homeostasis and neuroprotection. Unlike previous approaches, the advantages of the present strategy are obvious, as it allows us to modify the nonpolar tail, the carboxylated head or both ends of the molecule without repeating the whole synthetic sequence (about 26-34 steps according to the literature). Thus, the first total syntheses of NPD1 methyl ester epimer (which can also be considered as an enantiomer of AT-NPD1) and its n-3 docosapentaenoic acid derived analogue were achieved from a highly functionalized and late advanced pivotal intermediate. This innovative route may be easily adapted to gain access to other dihydroxylated metabolites and analogues of polyunsaturated fatty acids containing a conjugated E,E,Z-triene subunit. Different epimers/diastereoisomers may be obtained by purchasing the suitable optically pure (S)- and/or (R)-1,2,4-butanetriol(s) as a chiral pool for both stereogenic centers.

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Section: Introductionmentioning

confidence: 99%

A Versatile and Stereocontrolled Total Synthesis of Dihydroxylated Docosatrienes Containing a Conjugated E,E,Z‐Triene

Dayaker¹,

Balas²

2014

Chemistry A European J

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“…Leukotrienes which contain conjugated triene − and lipoxins 30-34 which contain conjugated tetraene are unstable compounds, and their syntheses require careful planning and execution. Oxoeicosanoids 11-14 present an additional degree of difficulty.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of a Potent Proinflammatory 5-Oxo-ETE and Its 6,7-Dihydro Biotransformation Product

et al. 1998

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The first total synthesis of a potent inflammatory mediator 5-oxo-6(E),8(Z),11(Z),14(Z)-eicosatetraenoic acid (5-oxo-ETE) 2 and its biotransformation product 6,7-dihydro-5-oxo-ETE 5 is reported. A convergent synthesis for the unstable title compounds is accomplished via two synthons, dithiolane aldehyde 13 and bisdienyl phosphonium bromide 19. The synthetic 5-oxo-ETE 2 and its 8,9-trans isomer 3 were used to unequivocally confirm the structure of the biologically derived mediators. In addition, using synthetic 6,7-dihydro-5-oxo-ETE 5 we have been able to identify in neutrophils the formation of 6,7-dihydro-5-oxo-ETE 5.

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“…The final conversion into the E or Z methylidyne derivatives of OS 23a, 23b and 25a, 25b was accomplished with tetrabutylammonium fluoride in anhydrous THF, in 77% and 78% yield respectively. [35][36][37] The OS analogues having the methylidyne function at the C-29 position of the squalene skeleton (29a and 29b) and the nor analogues (27a and 27b) (Scheme 6) were synthesized, although a survey of the literature showed no previously reported method. prop-2-ynyl]triphenylphosphonium bromide in anhydrous THF was reacted with an excess of butyllithium (see the Experimental section) and subsequently with 1-bromo-3-methylbut-2-ene, followed by the C 22 squalene aldehyde monobromohydrin 20 (Scheme 6).…”

Section: Synthesis Of 13-enynesmentioning

confidence: 99%

“…The final conversion into the methylidyne derivatives of OS 27a, 27b and 29a, 29b was accomplished with tetrabutylammonium fluoride in anhydrous THF, in 81% and 72% yield respectively. [35][36][37] The E : Z ratio was determined to be 1 : 1 by 1 H NMR analysis. 39 By comparing the synthesis of the two series of compounds, it can be observed that when the 18,19-double bond is trisubstituted, the E and Z isomers are obtained in similar amounts, while enynes are obtained with E stereoselectivity when the terminal isoprene chain is absent.…”

Section: Synthesis Of 13-enynesmentioning

confidence: 99%

Synthesis of (E)- and (Z)-29-methylidyne-2,3-oxidosqualene derivatives as inhibitors of liver and yeast oxidosqualene cyclase

Ceruti

Viola

Balliano

et al. 2002

J. Chem. Soc., Perkin Trans. 1

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The synthesis of (E )-and (Z )-29-methylidyne-2,3-oxidosqualene derivatives is described starting from the C 22 and C 17 squalene aldehyde monobromohydrins. The conversion was achieved by means of a Wittig reaction, followed by desilylation of the terminal acetylene. For trisubstituted 1,3-enynes, preliminary alkylation with a suitable allyl bromide was performed. A new procedure for the synthesis of squalene aldehyde C 27 , C 22 and C 17 monobromohydrins is also described. Some of the new compounds behaved as inhibitors of pig liver and yeast oxidosqualene cyclase and were time-dependent inhibitors of the animal enzyme.

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An efficient synthesis of leukotriene B4

Cited by 13 publications

References 6 publications

A Versatile and Stereocontrolled Total Synthesis of Dihydroxylated Docosatrienes Containing a Conjugated E,E,Z‐Triene

A Versatile and Stereocontrolled Total Synthesis of Dihydroxylated Docosatrienes Containing a Conjugated E,E,Z‐Triene

Total Synthesis of a Potent Proinflammatory 5-Oxo-ETE and Its 6,7-Dihydro Biotransformation Product

Synthesis of (E)- and (Z)-29-methylidyne-2,3-oxidosqualene derivatives as inhibitors of liver and yeast oxidosqualene cyclase

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