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Total synthesis of (±)-luminacin D
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Oehlrich, Daniel, Vidot, Sandrine M. E., Davies, Mark W., Clarkson, Guy J. and Shipman, Michael. (2007) Total synthesis of (±)-luminacin D. Tetrahedron, Vol.63 (No.22). pp. 4703-4711. ISSN 0040-4020
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Official URL: http://dx.doi.org/10.1016/j.tet.2007.03.096
Abstract
A 15-step synthesis of (+/-)-luminacin D from ethyl pent-2-ynoate is reported. The pivotal step involves the formation of the central C-2'/C-3' bond of the natural product by condensation of the titanium enolate derived from aromatic ketone 1 with aldehyde 2a. A remote asymmetric centre in aldehyde 2a exerts control over the stereochemical course of this reaction, with the major adduct (3a, 54% yield) possessing the required (2'S*,3'R*,5R*)-stereochemistry. This assignment was unambiguously established by X-ray crystallography of late stage synthetic intermediate, 17. Further manipulation of 3a (six steps) yielded synthetic ()-luminacin D spectroscopically identical to material isolated from Streptomyces sp. Mer-VD1207 by Naruse et al. (C) 2007 Elsevier Ltd. All rights reserved.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Chemistry |
| Journal or Publication Title: | Tetrahedron |
| Publisher: | Pergamon |
| ISSN: | 0040-4020 |
| Date: | 28 May 2007 |
| Volume: | Vol.63 |
| Number: | No.22 |
| Number of Pages: | 9 |
| Page Range: | pp. 4703-4711 |
| Identification Number: | 10.1016/j.tet.2007.03.096 |
| Status: | Peer Reviewed |
| Publication Status: | Published |
| Access rights to Published version: | Restricted or Subscription Access |
| URI: | http://wrap.warwick.ac.uk/id/eprint/31579 |
Data sourced from Thomson Reuters' Web of Knowledge
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