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Synthesis 1992; 1992(10): 957-958
DOI: 10.1055/s-1992-26277
short paper
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Asymmetric Synthesis of (-)-(E)-5-Hydroxy-5-isopropyl-3-hepten-2-one, A Cembrane-Derived Compound from Greek Tobacco

Makoto Shimazaki* , Akihiro Ohta
  • *Tokyo College of Pharmacy, 1432-1 Horinouchi, Hachioji, Tokyo 192-03, Japan
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Publication Date:
17 September 2002 (online)

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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.