90121-04-3Relevant academic research and scientific papers
Direct preparation of (Z,Z)-1,4-dienic units with a new C6 homologating agent: Synthesis of α-linolenic acid
Sandri,Viala
, p. 271 - 275 (2007/10/02)
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 transatalization. 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.
Total Stereospecific Synthesis of all cis-5,8,11,14,17-Eicosapentaenoic Acid (EPA)
Viala, Jacques,Sandri, Jacqueline
, p. 4897 - 4900 (2007/10/02)
Total stereospecific synthesis of EPA has been performed by a sequence of ozonolysis, selective reduction and Wittig reactions which affords the cis-skipped olefinic system.Versatile compound 4, readily prepared from dihydro anisole, allowed us to prepare the skipped dienic synthon 2 in high yield.Key Words: All cis-eicosapentanoic acid, EPA, cis-Wittig reaction, Ozonolysis.
