- A novel one-pot approach of hexahydropyrrolo[2,3-b ]indole nucleus by a cascade addition/cyclization strategy: Synthesis of (±)-esermethole
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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.
- Lucarini, Simone,Bartoccini, Francesca,Battistoni, Flavia,Diamantini, Giuseppe,Piersanti, Giovanni,Righi, Marika,Spadoni, Gilberto
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- Decarboxylative Synthesis of Functionalized Oxindoles via An Iron-Initiated Radical Chain Process and Application in Constructing Diverse Fused-Indoline Heterocycles
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Rapid construction of diverse fused-indoline?heterocycle (FIH) frameworks including high-value pyrroloindolines, furoindolines and thienoindolines in a two-step sequence has been described. The key to success hinges on the adoption of peresters as α-heteroatom alkyl radical precusors, which can smoothly react with N-arylacrylamides via a radical chain process initiated by inexpensive FeCl2?4H2O to afford the functionalized oxindoles, the key intermediates to FIH skeletons. The approach features operationally-simplicity, broad substrates scope and mild conditions. (Figure presented.).
- Cui, Zhihao,Du, Da-Ming
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supporting information
p. 93 - 99
(2017/10/24)
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- Palladium-catalyzed enantioselective domino heck-cyanation sequence: Development and application to the total synthesis of esermethole and physostigmine
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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.
- Pinto, Artur,Jia, Yanxing,Neuville, Luc,Zhu, Jieping
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p. 961 - 967
(2007/10/03)
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- Simple synthesis of racemic pyrrolo[2,3-b]indoles: Formal total synthesis of (±)-physostigmine
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Racemic pyrrolo [2,3-b]indoles were efficiently synthesized by the reaction of aromatic hydrazines with 4-chloro-2-methylbutanal. A formal total synthesis of physostigmine was achieved.
- Tsuji, Riichiro,Nakagawa, Masako,Nishida, Atsushi
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p. 587 - 593
(2007/10/03)
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