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Cicindeloine from Stenus cicindeloides - Isolation, Structure Elucidation, and Total Synthesis

Title 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.

Further data

Item Type: Article in a journal
Refereed: Yes
Additional notes: BAYCEER137426
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology > Former Professors
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology > Chair Animal Ecology II - Evolutionary Animal Ecology
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology > Former Professors > Chair Animal Ecology II - Univ.-Prof. Dr. Konrad Dettner
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Research Institutions
Research Institutions > Research Centres
Research Institutions > Research Centres > Bayreuth Center of Ecology and Environmental Research- BayCEER
Faculties
Result of work at the UBT: Yes
DDC Subjects: 500 Science
Date Deposited: 25 Jan 2018 13:55
Last Modified: 25 Jan 2018 13:55
URI: https://eref.uni-bayreuth.de/id/eprint/41479