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Multigram Scale (multigram + scale)
Selected AbstractsIlicic Acid as a Natural Quiron for the Efficient Preparation of Bioactive ,- and ,-EudesmolEUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 21 2009Alejandro F. Barrero Abstract An efficient procedure for the isolation of the sesquiterpene ilicic acid (3) on a multigram scale of extracts obtained from aerial parts of Inula viscosa (Asteraceae) was developed. Acid 3 is an appropriate starting material for short, enantiospecific syntheses of ,-eudesmol (1) and ,-eudesmol (2), natural products featuring significant antiangiogenic and anti-Alzheimer properties. Synthesis of 1 was achieved in six steps and the synthesis of 2 in seven, producing overall yields of 52 and 41,%, respectively.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) [source] Convenient General Asymmetric Synthesis of Roche Ester Derivatives through Catalytic Asymmetric Hydrogenation: Steric and Electronic Effects of LigandsADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 16 2008Cyrielle Pautigny Abstract An efficient and concise asymmetric hydrogenation of acrylate esters promoted by the cationic ruthenium monohydride complex [Ru(H)(,6 -cot)SYNPHOS]+BF4, is reported. A full investigation of the effects of catalyst precursors, solvents, temperature, hydrogen pressure, substrates as well as steric and electronic properties of ligands was carried out. The corresponding valuable Roche ester derivatives were obtained in good to excellent isolated yields and high enantioselectivities under mild conditions. The robustness and practicability of this highly enantioselective hydrogenation was demonstrated by the synthesis of the 3-hydroxy-2-methylpropanoic acid tert -butyl ester on a multigram scale, resulting in excellent yield and ee up to 94%. [source] Cyclopropyl Building Blocks for Organic Synthesis, 131.ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 15 2006Palladium-Catalyzed Bicyclization with Carbonyl Insertion of Alkenyl-Tethered Propargyl Carbonates Towards a Scalable Synthesis of Various 2-(Bicyclo[3.1.0]hex-1-yl)acrylates Abstract The Pd-catalyzed 5- exo-trig- 3 -exo-trig cascade cyclization of 1,6-enynes with a propargyl carbonate terminus offers the shortest synthetic route to variously substituted 2-(bicyclo[3.1.0]hex-1-yl)acrylates, a novel class of prospective monomers for low-shrinkage polymers. To apply this reaction to large-scale preparations of the said bicyclic acrylates, a flexible Pd catalyst system with tunable reactivity has been developed. The dependence of the product and diastereomer distribution on both the reaction conditions, including the type of palladium catalyst used, and on the nature of the substrate has been investigated. A variety of methyl 2-(bicyclo[3.1.0]hex-1-yl)acrylates and parent carboxylic acids as well as some of their derivatives of potential interest towards a technical application were prepared on a multigram scale. A general large-scale synthesis of the cyclization precursors bearing one or two carbonyl groups in the tether is also disclosed. [source] A Convergent Approach to Biocompatible Polyglycerol "Click" Dendrons for the Synthesis of Modular Core,Shell Architectures and Their Transport BehaviorCHEMISTRY - A EUROPEAN JOURNAL, Issue 30 2008Monika Wyszogrodzka Dipl.-Ing. Abstract Dendrimers are an important class of polymeric materials for a broad range of applications in which monodispersity and multivalency are of interest. Here we report on a highly efficient synthetic route towards bifunctional polyglycerol dendrons on a multigram scale. Commercially available triglycerol (1), which is highly biocompatible, was used as starting material. By applying Williamson ether synthesis followed by an ozonolysis/reduction procedure, glycerol-based dendrons up to the fourth generation were prepared. The obtained products have a reactive core, which was further functionalized to the corresponding monoazido derivatives. By applying copper(I)-catalyzed 1,3-dipolar cycloaddition, so-called "click" coupling, a library of core,shell architectures was prepared. After removal of the 1,2-diol protecting groups, water-soluble core,shell architectures 24,27 of different generations were obtained in high yields. In the structure,transport relationship with Nile red we observe a clear dependence on core size and generation of the polyglycerol dendrons. [source] | ||||||||||