Five Easy Pieces. The Total Synthesis of Phosphoiodyn A (and Placotylene A).
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.
Department of Chemistry, Stony Brook University , Stony Brook, New York 11794, United States.
David J
DJ
Galler
Department of Chemistry, Stony Brook University , Stony Brook, New York 11794, United States.
Kathlyn A
KA
Parker
D000114:Acetylene / Q000737:chemistry; D002454:Cell Differentiation; D053280:Diynes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D006847:Hydrocarbons, Iodinated / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D047494:PPAR delta / Q000819:agonists; D053279:Polyynes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
C000593350:14-iodotetradeca-13-en-3,5-diyn-1-ol; D053280:Diynes; D005233:Fatty Alcohols; D006847:Hydrocarbons, Iodinated; D009943:Organophosphorus Compounds; D047494:PPAR delta; C581059:phosphoiodyn A; D053279:Polyynes; D000114:Acetylene