On the structure of passifloricin A: asymmetric synthesis of the delta-lactones of (2Z,5S,7R,9S,11S)- and (2Z,5R,7R,9S,11S)tetrahydroxyhexacos-2-enoic acid.
Stereoselective syntheses of the delta-lactone of (2Z,5S,7R,9S,11S)-tetrahydroxyhexacos-2-enoic acid, the structure reported for passifloricin A, and of its (5R)-epimer are described. The creation of all stereogenic centers relied upon Brown's asymmetric allylation methodology. The lactone ring was created via ring-closing metathesis. The NMR data of both synthetic products, however, were different from those of the natural product. The published structure of passifloricin A is thus erroneous and will require further synthetic work to be unambiguously assigned. [structure: see text]
García-Fortanet
Jorge
J
Departamento de Química Inorgánica y Orgánica, Universidad Jaume I, Castellón, E-12080 Castellón, Spain.
Murga
Juan
J
Carda
Miguel
M
Marco
J Alberto
JA
D003500:Cyclization; D004951:Esterification; D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D011753:Pyrones / Q000737:chemistry*; D013237:Stereoisomerism
D005229:Fatty Acids, Monounsaturated; D007783:Lactones; D011753:Pyrones; C433046:passifloricin A