Stereoselective synthesis of the antiprotozoal lactone passifloricin A and seven isomers thereof.
The conjugated delta-lactone passifloricin A, a natural product with antiprotozoal activity, and seven isomers thereof have been synthesized in enantiopure form. It has been shown in this way that the proposed structure for the natural compound was erroneous. The correct structure is now evidenced. Key steps of the syntheses were asymmetric Brown-type aldehyde allylations and ring-closing metatheses.
Murga
Juan
J
Departamento de Química Inorgánica y Orgánica, Universidad Jaume I, E-12080 Castellón, Spain.
García-Fortanet
Jorge
J
Carda
Miguel
M
Marco
J Alberto
JA
D000981:Antiprotozoal Agents / Q000138:chemical synthesis*; D007536:Isomerism; D007783:Lactones / Q000138:chemical synthesis*; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000981:Antiprotozoal Agents; D007783:Lactones; D011753:Pyrones; C433046:passifloricin A