717124-38-4Relevant academic research and scientific papers
Ru(III)-Catalyzed Cyclization of Arene-Alkene Substrates via Intramolecular Electrophilic Hydroarylation
Youn, So Won,Pastine, Stefan J.,Sames, Dalibor
, p. 581 - 584 (2007/10/03)
(Matrix presented) We herein report that RuCl3/AgOTf has proven to be a hydroarylation catalyst with an efficiency and scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-ene substrates of diverse structural features, providing good to excellent yields of cyclization products (chromanes, tetralins, terpenoids, dihydrocoumarins).
A "Chiral Aldehyde" Equivalent as a Building Block Towards Biologically Active Targets
Trost, Barry M.,Crawley, Matthew L.
, p. 2237 - 2252 (2007/10/03)
Chiral γ-aryloxybutenolides, readily accessible through dynamic kinetic asymmetric transformation (DYKAT) of racemic acyloxybutenolides, were utilized as "chiral aldehyde" building blocks for intermolecular cycloadditions and Michael reactions. Unprecedented selectivity in trimethylenemethane cycloadditions with this building block allowed an efficient synthesis of a novel metabotropic glutamate receptor 1 antagonist in development by the Bayer corporation. These studies further inspired work that culminated in the total synthesis of (+)-brefeldin A, a natural product with a range of significant biological properties. All of the stereochemistry in this target molecule was derived from two palladium-catalyzed asymmetric allylic alkylation reactions. The trans-alkenes were synthesized by a Julia olefination and a ruthenium-catalyzed trans-hydrosilylation-protodesilylation protocol. The route to (+)-brefeldin A lends itself to analogue syntheses and was completed in 18 steps in 6% overall yield.
