6533b822fe1ef96bd127ddf0
RESEARCH PRODUCT
Stereoselective synthesis of the published structure of synargentolide A and of one of its stereoisomers
J. Garcia-fortanetJuan MurgaM. CardaJa Marcosubject
Asymmetric allylborationUNESCO::QUÍMICA:QUÍMICA::Química orgánica [UNESCO]Ring-closing metathesisUNESCO::QUÍMICA::Química orgánicaSynargentolide A:QUÍMICA [UNESCO]Synargentolide A ; Ring-closing metathesis ; Asymmetric allylboration ; Asymmetric dihydroxylationAsymmetric dihydroxylationdescription
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. Marco Ventura, Juan Alberto, alberto.marco@uv.es
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2005-01-01 |