1190409-97-2Relevant academic research and scientific papers
Stereocontrolled total syntheses of isodomoic acids G and H via a unified strategy
Denmark, Scott E.,Liu, Jack Hung-Chang,Muhuhi, Joseck M.
, p. 201 - 215 (2011/04/18)
Marine neuroexcitatory compounds isodomoic acids G and H were efficiently synthesized from a common intermediate using a silicon-based cross-coupling reaction. Dividing each target compound into the core fragment and the side-chain fragment enabled the synthesis to be convergent. The trans-2,3-disubstituted pyrrolidine core fragment was accessed through a diastereoselective rhodium-catalyzed carbonylative silylcarbocyclization reaction of a vinylglycine-derived 1,6-enyne. A stereochemically divergent desilylative iodination reaction was developed to convert the cyclization product to both E- and Z-alkenyl iodides, which would eventually lead to isodomoic acid G and isodomoic acid H, respectively. The late-stage alkenyl-alkenyl silicon-based cross-coupling reaction uniting the core alkenyl iodides and the side-chain alkenylsilanol was achieved under mild conditions. Finally, two mild deprotections afforded the target molecules.
Total syntheses of isodomoic acids G and H
Denmark, Scott E.,Liu, Jack Hung-Chang,Muhuhi, Joseck M.
supporting information; experimental part, p. 14188 - 14189 (2010/02/15)
(Chemical Equation Presented) The total syntheses of marine natural products belonging to the kainoid family, isodomoic acids G and H, are described. The strategic connection involves a sequential silylcarbocyclization/ silicon-based cross-coupling proces
