Next Article in Journal
Next Article in Special Issue
Previous Article in Journal
Previous Article in Special Issue
Mar. Drugs 2009, 7(4), 654-671; doi:10.3390/md7040654
Article

Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone

, ,
 and *
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)
View Full-Text   |   Download PDF [333 KB, uploaded 24 November 2009]
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 xestenone; marine norditerpene; total synthesis; structural determination
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


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.


Mar. Drugs EISSN 1660-3397 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert