A New Approach to Nicotine: Symmetry Consideration for Synthesis Design

A synthesis of nicotyrine (9), and hence formally racemic nicotine, was carried out by elaboration of the 1 : 1 adduct 2 of cycloocta‐1,5‐diene and chlorosulfonyl isocyanate (ClSO2NCO). Transformation of adduct 2 into carbamate 4 was followed by ozonolysis, tosylation, and NaH treatment, which led to pyrrolidinylpiperidinone 6. LiAlH4 Reduction, debenzylation, and aromatization yielded 2.