Asymmetric Synthesis of (-)-(E)-5-Hydroxy-5-isopropyl-3-hepten-2-one, A Cembrane-Derived Compound from Greek Tobacco

All articles of this category The lithiation of (+)- N , N -dimethyl-1-(2-methylsulfinylphenyl)-ethylamine ( 2 ) with butyllithium followed by reaction with unsymmetrical ketones gave the corresponding tert -alcohols with high diastereoselectivity. By following this procedure, ( R )-( E ) -5-hydroxy-5-isopropyl-3-hepten-2-one ( 1 ), isolated from the extract of Greek tobacco, was synthesized and the absolute configuration on the asymmetric carbon determined.