Enantioselective Synthesis of the Oxadecalin Core of Phomactin A via a Highly Stereoselective Diels−Alder Reaction
2001; American Chemical Society; Volume: 3; Issue: 19 Linguagem: Inglês
10.1021/ol0161357
ISSN1523-7060
AutoresSherry R. Chemler, Ulrich Iserloh, Samuel J. Danishefsky,
Tópico(s)Microbial Natural Products and Biosynthesis
ResumoPhomactin A (1) is a selective antagonist of platelet activating factor (PAF). Herein, we report our progress toward the construction of the oxadecalin core of 1. This route is based on the Diels−Alder cycloaddition of an appropriately functionalized vinyl pyran and a complementary dienophile. A model of this reaction involving 2 and maleic anhydride was conducted. Adduct 3 contains the correct stereochemical arrangements between functional groups necessary for gaining access to phomactin A.
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