Organocatalytic Enantioselective Friedel–Crafts Reaction of Phenanthrenequinones and Indoles

Molecules, Год журнала: 2025, Номер 30(1), С. 172 - 172

Опубликована: Янв. 4, 2025

An efficient stereoselective synthesis of 10-hydroxy-10-(1H-indol-3-yl)-9-(10H)-phenanthrene derivatives was realized through an organocatalyzed Friedel–Crafts reaction phenanthrenequinones and indoles using a (S,S)-dimethylaminocyclohexyl-squaramide as the catalyst. Under optimized conditions, desired chiral products were obtained in good yields (73–90%) with moderate to high ee values (up 97% ee). Two pairs synthesized enantiomers subjected evaluation their antiproliferative activities on four types human cancer cell lines one umbilical vein endothelial line CCK-8 assay. The results indicated that stereoselectivity had obvious impacts biological activity. (S)-4g found have optimal cytotoxicity against A549 safety profile for normal cells, which better than inhibitory activity positive control drug (doxorubicin).

Язык: Английский

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Highly Diastereoselective Synthesis of Oxindole‐Bearing Pyrroloindoline via Gold Catalyzed Carbophilic Carbene Transfer Reaction

Chemistry - A European Journal, Год журнала: 2025, Номер unknown

Опубликована: Март 12, 2025

Abstract A new type of gold catalyzed intermolecular dearomative cyclization reaction between diazo oxindole and tryptamine has been developed by utilizing the combination L 3 AuCl/Ag PO 4 ( =hexamethyl phosphane triamine) as catalyst. This method allows for facile preparation a series C‐3‐oxindole fused pyrroloindoline products in moderate to good yields with high diastereoselectivities. plausible mechanism, involving cascade process regioselective nucleophilic addition carbophilic carbenoid intermediate onto tryptamine, followed an intramolecular cyclization, proposed, which, diastereoselectivity is attributed preferred transition state. Moreover, three oxindole‐bearing indolo[2,3‐b] quinoline derivatives were synthesized through homotryptamine derivative 4a respective 3‐diazoindolin‐2‐one substrates using similar strategy. gram‐scale experiment successfully yielded 1.95 g aa 85 % yield diastereomeric ratio (dr) 10.4/1, ultimately enabling five‐step synthesis natural product (±)‐folicanthine.

Язык: Английский

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Asymmetric catalytic Friedel–Crafts alkylation with arenes and heteroarenes: construction of 3,3-disubstituted oxindoles

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(20), С. 5274 - 5283

Опубликована: Янв. 1, 2023

The asymmetric Friedel–Crafts alkylation of 3-bromo-3-substituted oxindoles with arenes and heteroarenes was achieved to synthesize enantioenriched C3-arylated oxindoles.

Язык: Английский

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Catalytic Asymmetric Reverse Prenylation of Indol-2-one Enabled a Synthesis of (−)-Debromoflustramine A

Organic Letters, Год журнала: 2023, Номер 25(38), С. 6949 - 6953

Опубликована: Сен. 15, 2023

A catalytic asymmetric nucleophilic reverse prenylation of indol-2-ones in situ generated from 3-bromooxindoles with prenyltributylstannane promoted by Ni(II)/chiral N,N'-dioxide was developed. This reaction provides facile access to C3 reverse-prenylated oxindoles good excellent enantioselectivities, which enabled the synthesis debromoflustramine five steps.

Язык: Английский

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