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Xenicane Natural Products: Biological Activity and Total Synthesis

[ Vol. 21 , Issue. 38 ]

Author(s):

Leo Betschart and Karl-Heinz Altmann   Pages 5467 - 5488 ( 22 )

Abstract:


The xenicanes are a large class of mostly bicyclic marine diterpenoids featuring a cyclononane ring as a common structural denominator. After a brief introduction into the characteristic structural features of xenicanes and some biogenetic considerations, the major focus of this review will be on the various biological activities that have been reported for xenicanes and on efforts towards the total synthesis of these structures. Several xenicanes have been shown to be potent antiproliferative agents in vitro, but activities have also been reported in relation to inflammatory processes. However, so far, data on the possible in vivo activity of xenicanes are lacking. The major challenge in the total synthesis of xenicanes is the construction of the nine-membered ring. Different strategies have been pursued to establish this crucial substructure, including Grob fragmentation, ring-closing olefin metathesis, or Suzuki cross coupling as the enabling transformations.

Keywords:

Xenicane, xeniane, diterpenoid, marine natural product, biological activity, total synthesis.

Affiliation:

Swiss Federal Institute of Technology (ETH) Z├╝rich, Department of Chemistry and Applied Biosciences, Institute of Pharmaceutical Sciences, HCI H405, Vladimir-Prelog- Weg 4, 8093 Zurich, Switzerland.



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