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Total synthesis of (+/-)-aspercyclide A and its C19 methyl ether. 2010

James L Carr, and Daniel A Offermann, and Mary D Holdom, and Philip Dusart, and Andrew J P White, and Andrew J Beavil, and Robin J Leatherbarrow, and Stephen D Lindell, and Brian J Sutton, and Alan C Spivey
Department of Chemistry, South Kensington campus, Imperial College, London, UK SW7 2AZ.

The total syntheses of (+/-)-aspercyclide A (1) and its C19 methyl ether (15a) featuring Heck-Mizoroki macrocyclisation to form the 11-membered (E)-styrenyl biaryl ether lactone core are described.

UI MeSH Term Description Entries
D007783 Lactones Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure. Large cyclic lactones of over a dozen atoms are MACROLIDES. Lactone
D008738 Methyl Ethers A group of compounds that contain the general formula R-OCH3. Ethers, Methyl
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D003500 Cyclization Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Cyclizations
D047028 Macrocyclic Compounds Cyclic compounds with a ring size of approximately 1-4 dozen atoms. Macrocycle Compounds,Spherands,Torands,Compounds, Macrocycle,Compounds, Macrocyclic
D018360 Crystallography, X-Ray The study of crystal structure using X-RAY DIFFRACTION techniques. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) X-Ray Crystallography,Crystallography, X Ray,Crystallography, Xray,X Ray Crystallography,Xray Crystallography,Crystallographies, X Ray,X Ray Crystallographies

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