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Β-Araneosene

Β-Araneosene

β-Araneosene is a molecule first isolated in 1975 from the mold Sordaria araneosa by Borschberg. This unprecedented diterpene framework was given the name “araneosene”. In 1976, the skeletal class was renamed to “dolabellane” due to the isolation of several compounds containing this framework found from the sea hare Dolabella californica.

Biosynthesis

The exact biosynthetic pathway of β-araneosene is not known; however, like other diterpenes, it is assumed to originate with geranylgeranyl pyrophosphate. The pyrophosphate dissociates to generate an allylic cation at the tail of the molecule. Next a cascade of cyclizations yields the stable β-araneosene-15-yl cation. Finally, elimination of the adjacent proton yields β–araneosene. It has been proposed that other diterpenes including fusicoccanes, dolastanes, and neodolabellanes also proceed through these intermediates.

β-Araneosene biosynthesis

References

References

  1. Rodríguez, Abimael. (1998). "The Structural Chemistry, Reactivity, and Total synthesis of Dolabellane Diterpenes". Tetrahedron.
  2. Rodríguez, Abimael D.. (28 May 2010). "Dolabellane-Type Diterpenoids with Antiprotozoan Activity from a Southwestern Caribbean Gorgonian Octocoral of the Genus". Journal of Natural Products.
  3. Dewick, Paul M.. (2009). "Medicinal natural products : A biosynthetic approach". A John Wiley & Sons.
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diterpenes cyclopentanes bicyclic-compounds
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