Cicindeloine from stenus cicindeloides - isolation, structure elucidation, and total synthesis
Cicindeloine from stenus cicindeloides - isolation, structure elucidation, and total synthesis
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
total synthesis, asymmetric synthesis, structure elucidation, natural products, alkaloids, schiff bases
2323-2330
Müller, Tobias
2cf2e278-0402-4480-880f-f84c02e30d78
Göhl, Matthias
c1a88862-272c-4660-8708-9cc8328f65d7
Lusebrink, Inka
f10f0d44-d917-4efc-a260-928fc1f06896
Dettner, Konrad
8fa1f390-dcd9-46bb-9c28-fb6a41ffa119
Seifert, Karlheinz
3028e3da-1efe-47b3-99a8-e92767ecd50d
April 2012
Müller, Tobias
2cf2e278-0402-4480-880f-f84c02e30d78
Göhl, Matthias
c1a88862-272c-4660-8708-9cc8328f65d7
Lusebrink, Inka
f10f0d44-d917-4efc-a260-928fc1f06896
Dettner, Konrad
8fa1f390-dcd9-46bb-9c28-fb6a41ffa119
Seifert, Karlheinz
3028e3da-1efe-47b3-99a8-e92767ecd50d
Müller, Tobias, Göhl, Matthias, Lusebrink, Inka, Dettner, Konrad and Seifert, Karlheinz
(2012)
Cicindeloine from stenus cicindeloides - isolation, structure elucidation, and total synthesis.
European Journal of Organic Chemistry, 2012 (12), .
(doi: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
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e-pub ahead of print date: 3 February 2012
Published date: April 2012
Keywords:
total synthesis, asymmetric synthesis, structure elucidation, natural products, alkaloids, schiff bases
Organisations:
Environmental
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Local EPrints ID: 343577
URI: http://eprints.soton.ac.uk/id/eprint/343577
ISSN: 1434-193X
PURE UUID: e55093c1-7654-427f-b1a4-4a6742904f0f
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Date deposited: 08 Oct 2012 15:15
Last modified: 14 Mar 2024 12:05
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Author:
Tobias Müller
Author:
Matthias Göhl
Author:
Inka Lusebrink
Author:
Konrad Dettner
Author:
Karlheinz Seifert
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