Stereochemical Determination of the Leupyrrins and Total Synthesis of Leupyrrin A<sub>1</sub>
2015-04-01T00:00:00Z (GMT) by
The stereochemical determination of the potent antifungal agents leupyrrin A<sub>1</sub> and B<sub>1</sub> and the total synthesis of leupyrrin A<sub>1</sub> are reported. The relative and absolute configuration was determined by a combination of high field NMR studies, molecular modeling, and chemical derivatization. The expedient total synthesis involves a one-pot sequential Zr-mediated oxidative diyne-cyclization/regioselective opening sequence for preparation of the unique dihydrofuran ring, a highly stereoselective one-pot approach to the butyrolactone, a challenging sp<sup>2</sup>–sp<sup>3</sup> Suzuki coupling and a high-yielding Shiina macrolactonization.