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

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

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MDPI and ACS Style

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

AMA Style

Ota K, Kurokawa T, Kawashima E, Miyaoka H. Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone. Marine Drugs. 2009; 7(4):654-671.

Chicago/Turabian Style

Ota, Koichiro; Kurokawa, Takao; Kawashima, Etsuko; Miyaoka, Hiroaki. 2009. "Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone." Mar. Drugs 7, no. 4: 654-671.

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