Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone |
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Authors: | Koichiro Ota Takao Kurokawa Etsuko Kawashima Hiroaki Miyaoka |
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Institution: | School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan; E-Mails: (K.O.); (E.K.) |
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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. |
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Keywords: | xestenone marine norditerpene total synthesis structural determination |
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