Efficient and Convenient Method for Synthesis of Solenopsin A and Its Analogues Using 1-Benzyl-2,6-dicyanopiperidine

Article abstract of DOI:10.1021/jo00222a033

An efficient synthetic sequence proposed here provides a new method for preparation of not only solenopsin A, i.e., trans-2-methyl-6-undecylpiperidine, but also coniine, i.e., 2-propylpiperidine, and other 2,6-dialkylpiperidine alkaloids: A reaction of 1-benzyl-2,6-dicyanopiperidine (1) with alkyl halides selectively gives 2-alkyl- and 2,6-dialkyl-1-benzyl-2,6-dicyanopiperidines (2 and 3), decyanation of which affords respectively 2-alkyl- and 2,6-dialkyl-1-benzylpiperidines (4 and 5) in high yields.