Reversal of nucleophilicity of enamides in water: Control of cyclization pathways by reaction media for the orthogonal synthesis of dihydropyridinone and pyrrolidinone Clausena alkaloids

Organic Letters

Volumn 10, Issue 12, 2008, Pages 2461-2464

  Yang, Luo ^a   Zheng, Qi Yu ^a   Wang, De Xian ^a   Huang, Zhi Tang ^a   Wang, Mei Xiang ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; ALKALOID; PYRIDONE DERIVATIVE; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CLAUSENA; CONFORMATION; CYCLIZATION; MEDICINAL PLANT; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKALOIDS; CLAUSENA; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PLANTS, MEDICINAL; PYRIDONES; PYRROLIDINONES; WATER;

EID: 48849106483     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800740h     Document Type: Article

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24. A single crystal of 2a was obtained from slow evaporation of the solvent from 2a solution in a mixture of ethyl acetate and hexane (1:1). To obtain single crystals of 4a and 4a′, recrystalization of a mixture of reaction products 4a and 4a′ (4a:4a′ = 3:7) in ethyl acetate gave pure 4a′ as solid. Slow evaporation of the solvent from 4a′ solution in a mixture of ethyl acetate and THF (1:1) gave single crystal of 4a′. The filtrate, which contains a mixture of 4a and 4a′ (4a:4a′ = 1:1) after recrystalization of 4a′, was subjected to the preparative HPLC with a C-18 column to give a fraction in which the ratio of 4a over 4a′ was 6:1. Slow evaporation of the solvent from its solution in a mixture of ethyl acetate and THF (1:1) gave single crystal of 4a.