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Synthesis 1993; 1993(4): 377-379
DOI: 10.1055/s-1993-25867
short paper
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An Efficient Stereocontrolled Synthesis of Methyl (9Z,11E,13S)-13-Hydroxyoctadeca-9,11-dienoate (Methyl Coriolate)

Denis Chemin* , Gérard Linstrumelle
  • *Ecole Normale Supérieure, Laboratoire de Chimie, 24 Rue Lhomond F-75231 Paris Cedex 05, France
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Publication Date:
17 September 2002 (online)

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An efficient synthesis of methyl (13S)-coriolate ( S )- 1b is accomplished by the palladium-catalyzed coupling of (1E,3S)-1-iodooct-1-en-3-ol [( S )-3] with methyl dec-9-ynoate (4) followed by selective reduction of the enyne ( S )- 2.