Total synthesis of (±)-luminacin D
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 0040-4020Full text not available from this repository.
Official URL: http://dx.doi.org/10.1016/j.tet.2007.03.096
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|
|Official Date:||28 May 2007|
|Number of Pages:||9|
|Page Range:||pp. 4703-4711|
|Access rights to Published version:||Restricted or Subscription Access|
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