Homofuran derivatives

This strategy to prepare rran.r,as-configurated functionalized dienes like 34 has elegantly been exploited for syntheses of HETEs (hydroxyeicosatetraenoic acids) and leukotrienes 27). These metabolites of arachidonic acid have received much attention due to thek biological activity. Syntheses of HETEs, for instance, follow the principle outlined in Eq. 12 with the acid catalysed ring opening of homofuran derivatives 36 to 37 as the stereoselective key step. 

Cyclopropanation of 1-oxy-1,3-dienes is not regioselective . However, certain homofuran derivatives can yield highly electrophilic dienes as demonstrated in equation 86 . This reaction has served as one of the basic steps in a synthesis of the arachidonic acid metabolite 5-HETE (5-hydroxyeicosatetraenoic acid) . 

The protolytic transformation of homofuran derivative 15 into methyl ( , )-6-oxohexa-2,4-dienoate is one of the key steps in a synthesis of the arachidonic acid metabolite 5-HETE. Activated, low acidity zeolites can be used to induce the isomerization of cyclo-propanes. " ... 

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