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Volumn , Issue 4, 2008, Pages 525-528

Highly efficient domino reaction for the synthesis of the erythrina and B-homoerythrina alkaloid skeleton

Author keywords

Domino reactions; Erythrina alkaloids; Indolizidine; Lactams; Lewis acids; Spiro compounds

Indexed keywords

BETA HOMOERYTHRINA ALKALOID; ERYTHRINA ALKALOID; LEWIS ACID; SPIRO COMPOUND; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CYCLIZATION; DRUG SYNTHESIS;

EID: 41049105631 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1032091 Document Type: Article

Times cited : (11)

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- General Procedure To a stirred solution of amine 2 (1.00 equiv) in MeCN (0.5 mL/mmol) was added dropwise at 0°C AlMe3 (2.00 M in toluene, 2.00 equiv, then In(OTf)3 (4-25 mol, and the ester 3 (1.00 equiv, and stirring was continued for 3-17 h at r.t. or the mixture was heated to 100-180°C under microwave irradiation. The reaction mixture was cooled to 0°C, TfOH (3.5 equiv) was added dropwise and stirring was continued for 5 h at r.t. Subsequently, the mixture was quenched by addition of sat. aq NaHCO3 at 0°C with stirring for 20 min. The mixture was extracted with EtOAc, the combined organic layers were washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was subjected to column chromatography to yield 38-99% of the spirocycle 4. Compound 4a: 1H NMR (300 MHz, DMSO, δ, 1.35-1.60 m, 5 H, 3-H2, 2-H2
- a, 8a-H), 2.39-2.48

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