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Updated: Mar 31, 2026

Chemical Triphosphorylation of Oligonucleotides
Published on: June 2, 2022
Five Easy Pieces. The Total Synthesis of Phosphoiodyn A (and Placotylene A)
David J Galler1, Kathlyn A Parker1
1Department of Chemistry, Stony Brook University , Stony Brook, New York 11794, United States.
Abstract:
The convergent total synthesis of the marine natural product phosphoiodyn A, a nanomolar agonist of human peroxisome proliferator-activated receptor delta (hPPARδ), was achieved in five steps total from commercially available and inexpensive starting materials. The synthesis relies on the unprecedented regioselective hydrozirconation of a terminal acetylene in the presence of a conjugated 1,3-diyne and on ammonolysis of a β-chlorophosphonic acid monoester. The scheme also provides the newly isolated placotylene A, an inhibitor of bone marrow-derived macrophage (BMM) differentiation.
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