at Google ScholarTitle data
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.
Vol. 12
(2012)
Issue 12
.
- pp. 2323-2330.
ISSN 1099-0690
DOI: https://doi.org/10.1002/ejoc.201101709
Abstract in another language
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.