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• Ota, K
• Kurokawa, T
• Kawashima, E
• Miyaoka, H
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• Kurokawa, T
• Kawashima, E
• Miyaoka, H
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• Kurokawa, T
• Kawashima, E
• Miyaoka, H

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Mar. Drugs 2009, 7(4), 654-671; doi:10.3390/md7040654

Article

Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone

Koichiro Ota, Takao Kurokawa, Etsuko Kawashima and Hiroaki Miyaoka*

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; in revised form: 19 November 2009 / Accepted: 23 November 2009 / Published: 24 November 2009

(This article belongs to the Special Issue Synthesis around Marine Natural Products)

Download PDF Full-Text [333 KB, uploaded 24 November 2009 12:14 CET]

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.

Keywords: xestenone; marine norditerpene; total synthesis; structural determination

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