Five Easy Pieces. The Total Synthesis of Phosphoiodyn A (and Placotylene A)
2015; American Chemical Society; Volume: 17; Issue: 22 Linguagem: Inglês
10.1021/acs.orglett.5b02642
ISSN1523-7060
AutoresDavid J. Galler, Kathlyn A. Parker,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoThe 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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