Stereodivergent Approach to Both C2,8a-syn and C2,8a-anti Relative Stereochemical Manifolds in the Lepadin Family via a TiCl₄-Promoted Aza-[3+3] Annulation

Abstract

Details in developing a stereodivergent approach to the lepadin family and establishing an entry to both C2,8a-syn and C2,8a-anti relative stereochemical manifolds through a common intermediate are described here. This works paves the foundation for constructing all members of the lepadin family, which consists of three subsets based on an array of interesting relative configurations. These efforts underline the prominence of aza-[3+3] annulation as a unified strategy in alkaloid synthesis.

titanium(IV) chloride - aza-[3+3] annulation - vinylogous amides - iminium ions - alkaloid synthesis - lepadin alkaloids - stereodivergent approach - episulfide contraction

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