Total Synthesis and Biological Activity of the Arachidonic
Acid Metabolite Hemiketal E2

Boer, Robert
E.; Giménez-Bastida, Juan Antonio; Boutaud, Olivier; Jana, Somnath; Schneider, Claus; Sulikowski, Gary A.

doi:10.1021/acs.orglett.8b01578.s001

ol8b01578_si_001.pdf (17.17 MB)

Total Synthesis and Biological Activity of the Arachidonic Acid Metabolite Hemiketal E₂

journal contribution

posted on 2018-06-18, 21:43 authored by Robert E. Boer, Juan Antonio Giménez-Bastida, Olivier Boutaud, Somnath Jana, Claus Schneider, Gary A. Sulikowski

The total synthesis of hemiketal E₂ (HKE₂) has been accomplished using a gold(I)-mediated cycloisomerization followed by oxidation of the enol ether product to introduce a unique keto-hemiketal, the core structure of HKE₂. Synthetic hemiketal E₂ reproduced biosynthetically derived HKE₂ in the inhibition of human platelet aggregation.