ChemInform Abstract: Conjugate Reduction Vicinal to Butadiene Tricarbonyl Iron Complexes. Application to the Synthesis of (.+-.)-6,7-Dihydro-LTB4 Methyl Ester.

Abstract

The conjugate reduction of enones vicinal to butadiene tricarbonyl iron complexes was best performed using Red-Al/CuBr/2-butanol in THF. This reaction was applied to α,β-unsaturated ketone 13 for the synthesis of three possible metabolites of LTB 4 (as their methyl esters 4a, 4b, 4c) generated via a 6,7-reductase pathway. Ketone 13 was synthesized in five steps starting from the organometallic complex 5. Conjugate reduction of 13 selectively saturated the 6,7 double bond to give ketone 14