Cargando…

Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone

Xestenone is a marine norditerpenoid found in the northeastern Pacific sponge Xestospongia vanilla. The relative configuration of C-3 and C-7 in xestenone was determined by NOESY spectral analysis. However the relative configuration of C-12 and the absolute configuration of this compound were not de...

Descripción completa

Detalles Bibliográficos
Autores principales: Ota, Koichiro, Kurokawa, Takao, Kawashima, Etsuko, Miyaoka, Hiroaki
Formato: Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2810225/
https://www.ncbi.nlm.nih.gov/pubmed/20098605
http://dx.doi.org/10.3390/md7040654
Descripción
Sumario:Xestenone is a marine norditerpenoid found in the northeastern Pacific sponge Xestospongia vanilla. The relative configuration of C-3 and C-7 in xestenone was determined by NOESY spectral analysis. However the relative configuration of C-12 and the absolute configuration of this compound were not determined. The authors have now achieved the total synthesis of xestenone using their developed one-pot synthesis of cyclopentane derivatives employing allyl phenyl sulfone and an epoxy iodide as a key step. The relative and absolute configurations of xestenone were thus successfully determined by this synthesis.