A Flexible, Stereoselective Approach to the Decorated cis-Hydrindane Skeleton: Synthesis of the Proposed Structure of Faurinone

A Flexible, Stereoselective Approach to the Decorated cis-Hydrindane Skeleton: Synthesis of the Proposed Structure of Faurinone

Two electrons, three new stereocentres: The cis‐hydrindane motif is found in a number of natural products that display important biological activity. A flexible, stereoselective approach to the framework has been developed that features highly diastereoselective, SmI2‐mediated cyclisations. The stra...

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Veröffentlicht in:Chemistry : a European journal 2008-08, Vol.14 (23), p.6862-6865
Hauptverfasser: Findley, Thomas J. K., Sucunza, David, Miller, Laura C., Davies, David T., Procter, David J.
Format: Artikel
Sprache:eng
Schlagworte:
Crystallography, X-Ray
Cyclization
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
hydrindane
Indans - chemistry
Models, Molecular
Molecular Structure
natural products
Organic Chemicals - chemistry
radicals
samarium
Stereoisomerism
total synthesis
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Beschreibung
Zusammenfassung:Two electrons, three new stereocentres: The cis‐hydrindane motif is found in a number of natural products that display important biological activity. A flexible, stereoselective approach to the framework has been developed that features highly diastereoselective, SmI2‐mediated cyclisations. The strategy has been exploited in the first synthesis of the proposed structure of faurinone, a sesquiterpene ketone isolated from Valeriana officinalis.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200800930