528867-44-9Relevant academic research and scientific papers
Stereoselective synthesis of the antiprotozoal lactone passifloricin A and seven isomers thereof
Murga, Juan,Garcia-Fortanet, Jorge,Carda, Miguel,Marco, J. Alberto
, p. 7277 - 7283 (2007/10/03)
The conjugated δ-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.
On the structure of passifloricin A: Asymmetric synthesis of the δ-lactones of (2Z,5S,7R,9S,11S)- and (2Z,5R,7R,9S,11S)-tetrahydroxyhexacos-2-enoic acid
Garcia-Fortanet, Jorge,Murga, Juan,Carda, Miguel,Marco, J. Alberto
, p. 1447 - 1449 (2007/10/03)
(Matrix presented) Stereoselective syntheses of the δ-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.
