Sp. Khanapure et al., TOTAL SYNTHESIS OF A POTENT PROINFLAMMATORY 5-OXO-ETE AND ITS 6,7-DIHYDRO BIOTRANSFORMATION PRODUCT, Journal of organic chemistry, 63(2), 1998, pp. 337-342
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 biotran
sformation product 6,7-dihydro-5-oxo-ETE 5 is reported. A convergent s
ynthesis for the unstable title compounds is accomplished via two synt
hons, dithiolane aldehyde 13 and bisdienyl phosphonium bromide 19. The
synthetic 5-oxo-ETE 2 and its 8,9-trans isomer 3 were used to unequiv
ocally confirm the structure of the biologically derived mediators. In
addition, using synthetic 6,7-dihydro-5-oxo-ETE 5 we have been able t
o identify in neutrophils the formation of 6,7-dihydro-5-oxo-ETE 5.