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Synthesis 1995; 1995(3): 271-275
DOI: 10.1055/s-1995-3906
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Direct Preparation of (Z,Z)-1,4-Dienic Units with a New C6 Homologating Agent: Synthesis of α-Linolenic Acid

Jacqueline Sandri, Jacques Viala*
  • *Laboratoire de Réactivité et Synthèse Organique, URA CNRS 1411, Université d’Aix-Marseille III, Boite D12, F-13397 Marseille Cedex 20, France, Fax +33(91)983865
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Publication Date:
31 December 2000 (online)

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Syntheses of two C6 homologating agents 2a and 2f are described. These agents allow direct access to the (Z,Z)-1,4-diene unit 3, a moiety present in a wide number of natural compounds. Compound 2a is prepared in 40% overall yield by selective epoxidation of methoxycyclohexa-1,4-diene followed by oxidative ring cleavage and transacetalization. Compound 2f is obtained in 90% yield by a one-step oxidative dimerization of phosphonium salt 1. A short synthetic application of these two new C6 homologating agents to the synthesis of α-linolenic acid is described.

C6 homologation - (Z,Z)-1,4-diene unit - acetal - Wittig - all (Z)-polyunsaturated fatty acids