Stereochemical determination of the leupyrrins and total synthesis of leupyrrin A1

Journal of the American Chemical Society
Daniel HerkommerDirk Menche

Abstract

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 sp(2)-sp(3) Suzuki coupling and a high-yielding Shiina macrolactonization.

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Citations

Aug 19, 2015·Nature Chemical Biology·Christopher T Walsh
Aug 4, 2016·Organic Letters·Sebastian ThiedeDirk Menche
Oct 27, 2016·Natural Product Reports·Zhong Jin
Jun 25, 2016·Beilstein Journal of Organic Chemistry·Sebastian BretzkeDirk Menche
Sep 15, 2017·Beilstein Journal of Organic Chemistry·Somaia Kamouka, Wesley J Moran
Aug 19, 2020·Chemical Communications : Chem Comm·Mingrui LiHe Huang
Jul 2, 2020·Chemistry : a European Journal·Paul R WosniokDirk Menche
Apr 4, 2021·International Journal of Molecular Sciences·Joonseong HurJaehoon Sim

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An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.