title: Efficient and scalable one-pot synthesis of 2,4-dienols from cycloalkenones: optimized total synthesis of valerenic acid.
abstract: A mild and selective one-pot procedure to provide 2,4-dienols from simple cycloalkenones in high yields is described. This transformation is based on the in situ formation of acid-labile allylic alcohols, which on treatment with trifluoroacetic acid undergo a formal [1,3]-hydroxy migration to form diastereo- and enantiomerically enriched 2,4-dienols. The usefulness of this protocol is demonstrated in a short synthesis of valerenic acid.
authors: Institute of Organic Chemistry, University of Vienna, Waehringer Strasse 38, 1090 Wien, Austria.
authors: Juergen
authors: J
authors: Ramharter
authors: Johann
authors: J
authors: Mulzer
mesh_terms: D003516:Cycloparaffins / Q000737:chemistry*; D007192:Indenes / Q000138:chemical synthesis*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D003516:Cycloparaffins; D007192:Indenes; D012717:Sesquiterpenes; C037133:valerenic acid