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Asymmetric Synthesis of the Tricyclic Core of Calyciphylline A ‑Type Alkaloids via Intramolecular [3 + 2] Cycloaddition

Author:Anonymous, Source:Original, Hits:1265, UpdateTime:2014-03-13

Asymmetric synthesis of the [5 − 6− 7] tricyclic system common to theCalyciphyllineA-type alkaloids is reported, featuring Overman rearrangement, Heck cyclization, intramolecular [3 + 2] cycloaddition, diastereoselective hydrogenation, and Claisen rearrangement as strategic events. The approach is capable of installing the crucial carbonyl functionality as well as multiple stereogenic centers within a congested polycyclic ring skeleton.