%0 Journal Article %A Herkommer, Daniel %A Thiede, Sebastian %A Wosniok, Paul R. %A Dreisigacker, Sandra %A Tian, Maoqun %A Debnar, Thomas %A Irschik, Herbert %A Menche, Dirk %D 2015 %T Stereochemical Determination of the Leupyrrins and Total Synthesis of Leupyrrin A1 %U https://acs.figshare.com/articles/journal_contribution/Stereochemical_Determination_of_the_Leupyrrins_and_Total_Synthesis_of_Leupyrrin_A_sub_1_sub_/2207974 %R 10.1021/jacs.5b01894.s001 %2 https://ndownloader.figshare.com/files/3843505 %K antifungal agents leupyrrin %K B 1 %K 1The stereochemical determination %K sequence %K stereoselective %K Suzuki %K sequential %K chemical derivatization %K Shiina macrolactonization %K approach %K preparation %K combination %K opening %K field NMR studies %K Leupyrrin %K butyrolactone %K oxidative %K modeling %K configuration %K sp %K Stereochemical Determination %K Total Synthesis %K synthesis %K dihydrofuran ring %X The stereochemical determination of the potent antifungal agents leupyrrin A1 and B1 and the total synthesis of leupyrrin A1 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 sp2–sp3 Suzuki coupling and a high-yielding Shiina macrolactonization. %I ACS Publications