104069-10-5Relevant articles and documents
A novel one-pot approach of hexahydropyrrolo[2,3-b ]indole nucleus by a cascade addition/cyclization strategy: Synthesis of (±)-esermethole
Lucarini, Simone,Bartoccini, Francesca,Battistoni, Flavia,Diamantini, Giuseppe,Piersanti, Giovanni,Righi, Marika,Spadoni, Gilberto
, p. 3844 - 3847 (2010)
A practical and efficient synthesis of 3-substituted hexahydropyrrolo[2,3- b]indole is described. The addition/cyclization of 3-substituted indoles with α,β-dehydroamino esters in the presence of a Lewis acid provides hexahydropyrrolo[2,3-b]indole adducts in good yields and stereoselectivities. This approach has been applied to the concise synthesis of esermethole employing an appropriately substituted indole and an N-acyl dehydroamino ester.
Palladium-catalyzed enantioselective domino heck-cyanation sequence: Development and application to the total synthesis of esermethole and physostigmine
Pinto, Artur,Jia, Yanxing,Neuville, Luc,Zhu, Jieping
, p. 961 - 967 (2007/10/03)
An efficient synthesis of functionalized 3-alkyl-3-cyanomethyl-2-oxindole 1 by a palladium-catalyzed domino Heck-cyanation reaction has been developed. Reaction of ortho-iodoanilide 5 with potassium ferro(II)cyanide, K 4[Fe(CN)6], dissolved in DMF in the presence of palladium acetate and sodium carbonate afforded oxindole 1 in good to excellent yields. An enantioselective domino Heck-cyanation process has been developed for the first time using (S)-DIFLUORPHOS as a chiral supporting ligand, and an enantioselectivity of up to 79% ee in the enantiomerically enriched oxindole was obtained under optimized conditions. A concise total synthesis of esermethole and physostigmine, powerful inhibitors of acetyl- and butyryl-cholinesterase, is documented.
