Synthesis of Substituted Indolizidines and Quinolizidines by Regioselective Intramolecular Modified Julia Olefination of Imides.

We report the synthesis of substituted indolizidines and quinolizidines using the modified Julia olefination previously developed on imides. The study focuses on the regioselectivity of this reaction on unsymmetrically substituted imides. The scope and regioselectivity of the reaction are presented here, and its utility as a tool for synthesizing natural products is demonstrated through the total synthesis of Pandalizine A.

Modified Julia Olefination on Anhydrides: Extension and Limitations. Application to the Synthesis of Maculalactone B.

The preparation of exo-enol esters from cyclic anhydrides is reported using a modified Julia olefination. The reaction is highly stereoselective. The Smiles rearrangement can be performed in a one-pot process, giving a straightforward access to exo-enol lactones. Furthermore, the reaction was extended to semistabilized sulfones, and this methodology was applied to the synthesis of maculalactone B.