We report the design, synthesis and validation of a bifunctional linchpin for three-component Type II Anion Relay Chemistry (ARC) fragment unions. The new linchpin undergoes nucleophilic addition at the aldehyde terminus under Felkin-Anh control to generate a syn-alkoxide. Solvent-triggered 1,4-Brook rearrangement subsequently promotes migration of the negative charge and generation of a dithiane-stabilized carbanion capable of capturing a terminating electrophile. The resulting three-component ARC adduct thus contains a stereodefined propionate subunit, which is a structural motif ubiquitous in polyketide natural products.

New aldehyde bifunctional linchpin for type II anion relay chemistry

248th National Meeting (2014)

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