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

Findley Thomas J. K. | Zendy; Sucunza David | Zendy; Miller Laura C. | Zendy; Davies David T. | Zendy; Procter David J. | Zendy

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

Author(s) -

Findley Thomas J. K.,

Sucunza David,

Miller Laura C.,

Davies David T.,

Procter David J.

Publication year - 2008

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.200800930

Subject(s) - stereoselectivity , sesquiterpene , ketone , stereochemistry , skeleton (computer programming) , structural motif , chemistry , combinatorial chemistry , computer science , organic chemistry , programming language , catalysis , biochemistry

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, SmI 2 ‐mediated cyclisations. The strategy has been exploited in the first synthesis of the proposed structure of faurinone, a sesquiterpene ketone isolated from Valeriana officinalis.

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