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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.