1020070-69-2Relevant academic research and scientific papers
Total syntheses of (±)-platencin and (-)-platencin
Nicolaou,Tria, G. Scott,Edmonds, David J.,Kar, Moumita
supporting information; experimental part, p. 15909 - 15917 (2010/01/30)
The secondary metabolites platensimycin and platencin, isolated from the bacterial strain Streptomyces platensis, represent a novel class of natural products exhibiting unique and potent antibacterial activity. Platencin, though structurally similar to platensimycin, has been found to operate through a slightly different mechanism of action involving the dual inhibition of lipid elongation enzymes FabF and FabH. Both natural products exhibit strong, broad-spectrum, Gram-positive antibacterial activity to key antibiotic resistant strains, including methicillin-resistant Staphylococcus aureus, vancomycin-intermediate S. aureus, and vancomycin-resistant Enterococcus faecium. Described herein are our synthetic efforts toward platencin, culminating in both racemic and asymmetric preparation of the natural product. The syntheses demonstrate the power of the cobalt-catalyzed asymmetric Diels-Alder reaction and the one-pot reductive rearrangement of [3.2.1] bicyclic ketones to [2.2.2] bicyclic olefins.
Total synthesis of (-)-platensimycin, a novel antibacterial agent
Ghosh, Arun K.,Xi, Kai
supporting information; experimental part, p. 1163 - 1170 (2009/08/15)
An enantioselective synthesis of platensimycin, a novel antibiotic natural product that inhibits bacterial β-ketoacyl-(acyl-carrier-protein) synthase (FabF), is described. Our synthetic strategy for the construction of the oxatetracyclic core involved an
Total synthesis of platencin
Nicolaou,Tria, G. Scott,Edmonds, David J.
supporting information; experimental part, p. 1780 - 1783 (2009/02/06)
(Chemical Equation Presented) The asymmetric total synthesis of the newly discovered and potent antibiotic platencin has been achieved. The approach makes use of an asymmetric Diels-Alder reaction, a gold(I)-catalyzed cyclization, and a homoallyl radical rearrangement to forge the polycyclic architecture of this intriguing target (see scheme, SEM=2-(trimethylsilyl)ethoxymethyl).
