Stereoselective synthesis of the published structure of synargentolide A and of one of its stereoisomers
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Stereoselective synthesis of the published structure of synargentolide A and of one of its stereoisomers

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Stereoselective synthesis of the published structure of synargentolide A and of one of its stereoisomers

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García-Fortanet, Jorge; Murga, Juan; Carda, Miguel; Marco Ventura, Juan Alberto
Aquest document és un/a article publicat, creat/da en: 2005
A stereoselective synthesis is described of the structure published for the naturally occurring synargentolide A, an α,β-unsaturated lactone. The key steps of the synthesis were a Brown´s asymmetric allylation and a ring closing metathesis. The spectroscopic data of the synthetic product were very close to those of the natural product but did not exactly match them. An epimer of the published structure was then synthesized according to a similar strategy. Again, the data of the synthetic product did not match those reported for the natural product. It is thus likely that the actual structure of synargentolide A differs from the published one in more than mere stereochemical aspects.

    GARCÍA-FORTANET, Jorge ; Murga, Juan ; Carda, Miguel ; Marco Ventura, Juan Alberto, 2005, Stereoselective synthesis of the published structure of synargentolide A and of one of its stereoisomers, Arkivoc, vol. 2005, no. IX, p. 175-188
http://www.arkat-usa.org/get-file/19597/
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