91817-43-5Relevant 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.
Divergent reactivity in tandem reduction - Michael ring closures of five- and six-membered cyclic enones
Bunce, Richard A.,Nammalwar, Baskar,Slaughter, LeGrande M.
experimental part, p. 854 - 860 (2009/12/24)
(Chemical Equation Presented) In this study, methyl (±)-1-(2- nitrobenzyl)-4-oxo-2-cyclohexene-1-carboxylate and methyl (±)-(2- nitrobenzyl)-4-oxo-2-cyclopentene-1-carboxylate were prepared and subjected to reductive cyclization under dissolving metal conditions. The two reactants showed divergent behavior with the six-ring substrate reacting at the ester carbonyl and the five-ring substrate closing on the enone double bond. The difference in reactivity is attributed to the conformational flexibility, relative reactivity, and steric environment of C4-substituted six- and five-membered cyclic enones.
Tricarbonylcyclohexadienyliron Complexes as Aryl Equivalents: A Formal Synthesis of (+/-)-O-Methyljoubertiamine
Pearson, Anthony J.,Richards, Ian C.,Gardner, Derek V.
, p. 3887 - 3891 (2007/10/02)
The use of tricarbonyl(4-methoxycyclohexadienyl)iron hexafluorophosphate 1b as a synthetic equivalent of the p-anisyl cation for a formal synthesis of (+/-)-O-methyljoubertiamine is described.
