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Recent Synthetic Studies Leading to Structural Revisions of Marine Natural Products
Mar. Drugs 2009, 7(4), 654-671; doi:10.3390/md7040654

Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone

School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
* Author to whom correspondence should be addressed.
Received: 2 November 2009 / Revised: 19 November 2009 / Accepted: 23 November 2009 / Published: 24 November 2009
(This article belongs to the Special Issue Synthesis around Marine Natural Products)
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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.
Keywords: xestenone; marine norditerpene; total synthesis; structural determination xestenone; marine norditerpene; total synthesis; structural determination
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Ota, K.; Kurokawa, T.; Kawashima, E.; Miyaoka, H. Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone. Mar. Drugs 2009, 7, 654-671.

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