Hemiketal D2 and E2 are eicosanoids identified by Schneider and coworkers in 2011. These novel arachidonic acid metabolites are cross-over products of the enzymes 5-LOX and COX-2 previously assumed to be operating independently in the biosynthesis of leukotrienes and prostaglandins, respectively. It was shown that hemiketals stimulate angiogenesis of vascular endothelial cells, suggesting these compounds may be involved in inflammation and tissue repair. As the enzymatic production of these compounds is low yielding, total synthesis provides an attractive option for their production for further study. Presented herein is the total synthesis of HKE2 and efforts toward HKD2, featuring a metal promoted cycloisomerization-oxidation sequence to form the unique keto hemiketal moiety. 

Total synthesis of HKD<sub>2</sub> and HKE<sub>2</sub>: Hemiketal-containing arachidonic acid metabolites

248th National Meeting (2014)

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Total synthesis of HKD2 and HKE2: Hemiketal-containing arachidonic acid metabolites

Total synthesis of HKD₂ and HKE₂: Hemiketal-containing arachidonic acid metabolites