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Müller, Tobias ; Göhl, Matthias ; Lusebrink, Inka ; Dettner, Konrad ; Seifert, Karlheinz:
Cicindeloine from Stenus cicindeloides - Isolation, Structure Elucidation, and Total Synthesis.
In: European Journal of Organic Chemistry.
Bd. 12
(2012)
Heft 12
.
- S. 2323-2330.
ISSN 1099-0690
DOI: https://doi.org/10.1002/ejoc.201101709
Abstract
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.