68085-53-0Relevant academic research and scientific papers
Regioselective entry to bromo-γ-hydroxybutenolides: Useful building blocks for assemblying natural product-like libraries
Aquino,Bruno,Riccio,Gomez-Paloma
, p. 4831 - 4834 (2007/10/03)
(Chemical Equation Presented) We report a regioselective entry to 3-bromo- and 4-bromo-5-hydroxy-5H-furan-2-ones by photooxidation of 3-bromofuran with a singlet oxygen in the presence of a suitable base. By this procedure, a variety of 3-substituted γ-hydroxybutenolides have become for the first time easily accessible. Strategies employing these highly functionalized building blocks for the preparation of focused libraries of natural-like molecules are also discussed.
Total synthesis of manoalide
Coombs,Lattmann,Hoffmann
, p. 1367 - 1371 (2007/10/03)
Me3Al/AlCl3-mediated hetero-Diels-Alder (HDA) additions of 2-silyloxy-1,3-dienes to formylated butenolide 6 containing a protected hydroxy function afford, in one step, a variety of pyranofuranones including manoalide precursor 16, which is a stable monoprotected seco-manoalide.
Non-stabilized azomethine ylides in [3 + 2] cycloadditions. Pyrrolidinylfuranones from (5S)-5-menthyloxy-4-vinylfuran-2(5H)-one
Gerlach, Kai,Hoffmann,Wartchow
, p. 3867 - 3872 (2007/10/03)
Upon sonication with lithium fluoride in acetonitrile N-benzyl-N-methoxymethyl(trimethylsilylmethyl)amines 9a-c undergo chemoselective 1,3-dipolar cycloaddition with 4-vinylfuranones 2 and 6 to afford pyrrolidinylfuranones 10, 11a-c and 12a-c. The stereochemistry is assigned by X-ray analyses and proton NMR data comparison of related oxiranylfuranone 13.
