Synthesis of the Marine Compound (2R,5Z,9Z)-2-Methoxyhexacosa-5,9-dienoic Acid via a Lipase-Catalyzed Resolution and a Novel O-Alkylation Protocol

 

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Abstract

The title compound has been synthesized by a facile route starting from 4-pentyn-1-ol. The enantioselectivity was attained by a strategy involving a lipase-catalyzed acetylation of a solid-phase immobilized long chain α-hydroxy acid. Another important feature of the synthesis was the formulation of an efficient HgO-catalyzed O-methylation of the α-hydroxy acids which proceeded without any racemization. The alkylation protocol was also highly efficient for selective mono-methylation/benzylation of symmetrical diols.

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