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