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

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

doi:10.1021/acs.orglett.8b01578

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

Org Lett. 2018 Jul 6;20(13):4020-4022. doi: 10.1021/acs.orglett.8b01578. Epub 2018 Jun 19.

Authors

Robert E Boer¹, Juan Antonio Giménez-Bastida², Olivier Boutaud², Somnath Jana¹, Claus Schneider², Gary A Sulikowski^{1

2}

Affiliations

¹ Department of Chemistry , Vanderbilt University, Vanderbilt Institute of Chemical Biology Nashville , Tennessee 37232 , United States.
² Department of Pharmacology , Vanderbilt University, Vanderbilt Institute of Chemical Biology Nashville , Tennessee 37232 , United States.

Abstract

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.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Arachidonic Acid / chemistry*
Blood Platelets
Humans
Molecular Structure
Oxidation-Reduction

Substances

Arachidonic Acid

Abstract

Publication types

MeSH terms

Substances

Grants and funding