|Müller, T; Göhl, M; Lusebrink, I; Dettner, K; Seifert, K: Cicindeloine from Stenus cicindeloides – Isolation, Structure Elucidation, and Total Synthesis, European Journal of Organic Chemistry, 12, 2323-2330 (2012)|
The new piperideine alkaloid cicindeloine (3) was isolated from the pygidial glands of the beetles Stenus cicindeloides and Stenus solutus. The structure and absolute configuration of 3 were elucidated by NMR spectroscopy and asymmetric synthesis, respectively. A very efficient gram-scale synthesis of 3 was developed using an intramolecular aza-Wittig reaction as the final step. The synthetic route is comprised of 12 steps and proceeds in 20 % total yield. Nine of the 12 steps were conducted without column chromatography.