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Synthesis of the reported structure of piperazirum using a nitro-Mannich reaction as the key stereochemical determining step.

Anderson, JC; Kalogirou, AS; Porter, MJ; Tizzard, GJ; (2013) Synthesis of the reported structure of piperazirum using a nitro-Mannich reaction as the key stereochemical determining step. [Letter]. Beilstein Journal of Organic Chemistry , 9 1737 - 1744. 10.3762/bjoc.9.200. Green open access

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Abstract

Piperazirum, isolated from Arum palaestinum Boiss, was originally assigned as r-3,c-5-diisobutyl-c-6-isopropylpiperazin-2-one. The reported structure was synthesised diastereoselectively using a key nitro-Mannich reaction to set up the C5/C6 relative stereochemistry. The structure was unambiguously assigned by single crystal X-ray diffraction but the spectroscopic data did not match those reported for the natural product. The structure of the natural product must therefore be revised.

Type: Article
Title: Synthesis of the reported structure of piperazirum using a nitro-Mannich reaction as the key stereochemical determining step.
Location: Germany
Open access status: An open access version is available from UCL Discovery
DOI: 10.3762/bjoc.9.200
Publisher version: http://dx.doi.org/10.3762/bjoc.9.200
Language: English
Additional information: © 2013 Anderson et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)
Keywords: alkaloid, aza-Henry, natural products, nitro-Mannich, piperazinone, stereoselective synthesis
UCL classification: UCL
UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/1413075
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