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Saturated bicycles, containing nitrogen atom on the bridgehead, such as pyrrolizidines and indolizidines, are commonly occurring structural motifs within natural products possessing a wide range of biological activities. Herein we report the synthesis of 1-Me derivatives of alkaloid isoretronecanol and the corresponding indolizidine. The aza-Cope-Mannich tandem reaction was envisioned as a key step in the sequence to the requisite bicyclic carcass.