ChemInform Abstract: An Efficient New Route to Plasmenyl‐Type Lipids: Synthesis and Cytotoxicity of a Plasmenylcholine Analogue of the Antitumor Ether Lipid ET‐18‐OMe.

Abstract

An Efficient New Route to Plasmenyl-Type Lipids: Synthesis and Cytotoxicity of a Plasmenylcholine Analogue of the Antitumor Ether Lipid ET-18-OMe.-Key step in the synthesis of the novel plasmenylcholine analogue (IX) is the Z-selective lithiation-alkylation of vinyldioxane (V) under Barbier-type reaction conditions to give enol (VII). Plasmenylcholine analogue (IX) possesses cytotoxic activity comparable to ET-18-OMe and ET-16-OMe. Interestingly, the Tbs analogue (X) of vinyldioxane (V) provides the enols (XII)/(XIII) with E-selectivity during Barbier-type lithiation-alkylation. -(SHIN, JUNHWA; QUALLS, MARQUITA M.; BOOMER, JEREMY A.; ROBARGE, JASON; THOMPSON, DAVID H.; J.