Stereochemical evaluation of sesquiterpene quinones from two sponges of the genus Dactylospongia and the implication for enantioselective processes in marine terpene biosynthesis

@article{Yong2008StereochemicalEO,
  title={Stereochemical evaluation of sesquiterpene quinones from two sponges of the genus Dactylospongia and the implication for enantioselective processes in marine terpene biosynthesis},
  author={Ken W L Yong and Aroon Jankam and John N A Hooper and Apichart Suksamrarn and Mary J. Garson},
  journal={Tetrahedron},
  year={2008},
  volume={64},
  pages={6341-6348}
}
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References

SHOWING 1-10 OF 34 REFERENCES
Total Synthesis of the Marine Sesquiterpene Quinones Hyatellaquinone and Spongiaquinone
The synthesis of the marine sesquiterpene quinone (+)-hyatellaquinone (1) was achieved starting from the sesquiterpene aldehyde (+)-albicanal ((+)-3) (Schemes 3 and 4). Coupling of (+)-albicanal with
5-Epi-isospongiaquinone, a new sesquiterpene/quinone antibiotic from an Australian marine sponge, Spongia hispida.
TLDR
An Australian marine sponge, Spongia hispida, has been found to contain a new sesquiterpene/quinone identified by detailed spectroscopic analysis and chemical derivatization as the antibiotic 5-epi-isospongiaquinone, which was speculated to be an artifact of the isolation process.
Biosynthesis of monoterpenes. Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (-)-pinene cyclases from sage.
TLDR
Results indicate that the alternate substrates are ionized by the cyclases prior to their achieving the optimum orientation for bicyclization.
Merosesquiterpenes from two sponges of the genus Dysidea.
TLDR
The chemical study of two sponges of the genus Dysidea collected in the Gulf of California has led to the isolation of the new merosesquiterpenes 20-O-acetyl-21-hydroxy-ent-isozonarol, which showed cytotoxic activity against three human tumor cell lines.
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