Enantioselective total synthesis of 1-epi-pathylactone A.
[structure: see text]. The first enantioselective total synthesis of 1-epi-pathylactone A, 3, has been accomplished using a PhI(OAc)2-mediated domino reaction as a key step. No diastereomeric separation was required throughout the whole synthetic scheme presented in this paper. Comparison of 1H and 13C NMR spectral data of the synthetic product with the reported spectral data of natural pathylactone A, coupled with an X-ray crystallographic analysis, led to the conclusion that the C1 configuration in the original paper was erroneously ascribed to (R).
Chanu
Angéline
A
Institut de Chimie des Substances Naturelles, CNRS F-91198 Gif-sur-Yvette, France.
Safir
Imad
I
Basak
Ramkrishna
R
Chiaroni
Angèle
A
Arseniyadis
Siméon
S
D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C519471:1-epi-pathylactone A; D001952:Bridged-Ring Compounds; D007783:Lactones; D012717:Sesquiterpenes; D013141:Spiro Compounds