Selective conversion of an enantioenriched cyclononadienone to the xeniolide, xenibellol, and florlide cores: an integrated routing strategy

Members of the xenicane superfamily induce a variety of biological responses in vitro. In order to enable a better understanding of the function of these substances, we have developed a strategy that integrates the synthetic routes to many of its members. The core ring systems of the xeniolide, xeni...

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Bibliographic Details
Published in:Tetrahedron letters 2011-01, Vol.52 (2), p.325-328
Main Authors: Drahl, Michael A., Akhmedov, Novruz G., Williams, Lawrence J.
Format: Article
Language:English
Subjects:
Biosynthesis
Diterpene
Integrated routing
Synthesis
Transannular
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Summary:Members of the xenicane superfamily induce a variety of biological responses in vitro. In order to enable a better understanding of the function of these substances, we have developed a strategy that integrates the synthetic routes to many of its members. The core ring systems of the xeniolide, xenibellol, and florlide natural products were constructed stereoselectively from an enantioenriched cyclononadienone. The use of the cyclononadiene scaffold, reagent-controlled transannulations, and the parallels of these transformations to possible biosynthetic pathways of the natural product classes are discussed.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.11.050