%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