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The first asymmetric synthesis and configurational elucidation of (−)-cephalezomine G was achieved. The highly functionalized Cα-substituted proline derivative was prepared from d-proline as the only chiral source via a C → N → C chirality transfer method consisting of stereoselective N-allylation and [2,3]-Stevens rearrangement. The azaspiranic tetracyclic backbone was constructed using ring-closing metathesis and the Friedel–Crafts reaction. Two contiguous hydroxyl groups were introduced in the later stages.