title: Total synthesis and absolute configuration of the marine norditerpenoid xestenone.
abstract: 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.
authors.affiliation: School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, Japan. otak@toyaku.ac.jp
authors.forename: Koichiro
authors.initials: K
authors.lastname: Ota
authors.forename: Takao
authors.initials: T
authors.lastname: Kurokawa
authors.forename: Etsuko
authors.initials: E
authors.lastname: Kawashima
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Miyaoka
mesh_terms: D000818:Animals; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D047131:Xestospongia / Q000737:chemistry*
chemical_list: D004224:Diterpenes; C550266:xestenone