Stereoselective synthesis of 10,11-dihydro-leukotriene B4 and related metabolites

Article abstract of DOI:10.1016/S0040-4039(98)01346-X

Nickel-catalyzed coupling reaction of cis bromide 6 and the borates 5a and 5b, prepared from the boronate esters 4a and 4b, proceeded stereospecifically to furnish 7a and 7b, which upon treatment with Bu₄NF in THF afforded 10,11-dihydro-leukotriene B₄ (1) and the B₃ (2), respectively. In a similar way, EE ether 19 and rac-4a gave 20 and the subsequent functional group transformation afforded 10,11-dihydro-12-oxo-LTB₄ (3).