Asymmetric synthesis of (-)-(E)-5-hydroxy-5-isopropyl-3-hepten-2-one, a cembrane-derived compound from Greek tobacco

Article abstract of DOI:10.1055/s-1992-26277

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-ones (1), isolated from the extract of Greek tobacco, was synthesized and the absolute configuration on the asymmetric carbon determined.