From Stereodefined Cyclobutenes to Dienes: Total Syntheses of Ieodomycin D and the Southern Fragment of Macrolactin A.
A copper-promoted flexible synthesis of cyclobutenes carrying simple alkyl chains, enabling even the most hindered nucleophiles to be employed, has been developed. The versatility of this approach was exemplified by a short total synthesis of ieodomycin D and a straightforward preparation of the southeastern fragment of macrolactin A. The latter features a late-stage, double cyclobutene electrocyclic ring opening that directly delivers a bis-diene of defined geometry.
University of Vienna , Faculty of Chemistry, Institute of Organic Chemistry, Währinger Straße 38, 1090 Vienna, Austria.
Caroline
C
Souris
University of Vienna , Faculty of Chemistry, Institute of Organic Chemistry, Währinger Straße 38, 1090 Vienna, Austria.
Antonio
A
Misale
University of Vienna , Faculty of Chemistry, Institute of Organic Chemistry, Währinger Straße 38, 1090 Vienna, Austria.
Yong
Y
Chen
University of Vienna , Faculty of Chemistry, Institute of Organic Chemistry, Währinger Straße 38, 1090 Vienna, Austria.
Marco
M
Luparia
University of Vienna , Faculty of Chemistry, Institute of Organic Chemistry, Währinger Straße 38, 1090 Vienna, Austria.
Nuno
N
Maulide
D003503:Cyclobutanes / Q000737:chemistry*; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011090:Polyenes / Q000737:chemistry; D013237:Stereoisomerism
D003503:Cyclobutanes; D005231:Fatty Acids, Unsaturated; C561379:Ieodomycin A; D018942:Macrolides; D011090:Polyenes; C453562:macrolactin A