218898-63-6Relevant academic research and scientific papers
Stereoselective synthesis of the C1-C5 dienoic sub-unit of bafilomycins via a γ-sulfonyl-δ-lactone intermediate
Demont, Emmanuel,Lopez, Roman,Férézou, Jean-Pierre
, p. 1223 - 1226 (2007/10/03)
A convergent and highly diastereoselective route for the synthesis of the (E,E)-2-methoxypent-2,4-dienoic ester sub-unit of bafilomycins has been developed through a Julia-Lythgoe olefination strategy. Condensation of an easily available γ-dimethoxy δ-carboxy secondary sulfone precursor on model aldehydes was shown to deliver either acyclic hydroxyesters or δ-lactones depending on the quenching conditions. The subsequent reductive elimination reaction was studied on both types of condensation products using Na/Hg as well as SmI2/ HMPA conditions and proved highly stereoselective, particularly with Na/Hg.
