Synthesis of oxylipids via a boronic ester cycloetherification approach

Abstract

Deprotonated trimethylsilylethanol can be used as a nucleophile in Matteson homologations. This O-protection group is stable under the usual reaction conditions of the Matteson reaction, but after two further homologation steps it is automatically cleaved off and cycloetherification can take place, giving rise to substituted tetrahydrofurans in a highly stereoselective fashion. This elegant protocol was used in the synthesis of various oxylipids.