- Metalation of pi-deficient heterocycles a facile synthesis of cerpegin
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The first total synthesis of the naturally occuring cerpegin is described. Metalation of a pyridine derivative has been used in the key step.
- Guillier, Fabricee,Nivoliers, Francois,Bourguignon, Jean,Dupas, Georges,Marsais, Francis,Godard, Alain,Queguiner, Guy
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- One-pot three steps synthesis of cerpegin
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Cerpegin 1 was synthesized in a one-pot reaction at room temperature catalysed by cesium carbonate with an overall of 75% yield. 3-Hydroxy-3-methyl-2-butanone 2 reacted with diethyl malonate 3 to give 2-ethoxycarbonyl-3,4,4-trimethyl-2-buten-4-olide 4. Then 4 with s-triazine gave to 1,1-dimethylfuro[3,4-c]pyridine-3,4(1H, 5H)-dione 5 and which was alkylated with methyliodide to cerpegin.
- Villemin, Didier,Liao, Liang
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- Convenient synthesis of cerpegin
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A convenient procedure for the preparation of cerpegin is described. Taylor & Francis Group, LLC.
- Avetisyan, Aida,Karapetyan, Lousine
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- 'One-pot' four-step synthesis of cerpegin
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Cerpegin (1) was synthesized through a 'one-pot' reaction in 71% overall yield. Lithiation of commercially available 2-methoxynicotinic acid (2) as its lithium salt using LTMP, followed by addition of acetone at low temperature and a specific acidic treatment of the intermediate 3 thus obtained, gave the 1,1-dimethyl-3,4-dioxo-1,3,4,5-tetrahydrofuro[3,4-c]pyridine (4). The latter was finally selectively alkylated using methyl iodide and caesium carbonate to afford cerpegin (1).
- Lazaar, Jalal,Hoarau, Christophe,Mongin, Florence,Trécourt, Francois,Godard, Alain,Quéguiner, Guy,Marsais, Francis
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- Two versatile routes towards Cerpegin and analogues: Applications of a one pot reaction to new analogues of Cerpegin
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Simple and efficient routes to the natural alkaloid Cerpegin and new analogues are described herein. In a first approach, we extend the scope of a one pot three steps reaction, which permits the synthesis of new analogues of Cerpegin, substituted in different ways. In a second line of approach, we present an unprecedented synthesis of Cerpegin and analogues where methylfuranones are condensed with dimethylformamide diethylacetal (DMFDEA) to yield enaminolactone esters, which react easily with various primary amines affording Cerpegin and new analogues. We applied this second approach to the synthesis of new bis-Cerpegins and N-amino-Cerpegins. Most of the syntheses are performed under environmental friendly conditions.
- Villemin, Didier,Cheikh, Nawel,Liao, Liang,Bar, Nathalie,Lohier, Jean-Fran?ois,Sopkova, Jana,Choukchou-Braham, Noureddine,Mostefa-Kara, Bachir
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experimental part
p. 4906 - 4918
(2012/07/28)
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- Alternative synthesis of a pyridone alkaloid, cerpegin
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A new pyridone alkaloid, cerpegin was synthesized starting from (-)-carvone.
- Matsuo, Keizo
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p. 1191 - 1195
(2007/10/03)
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- Synthesis of a pyridone alkaloid, cerpegin
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A new pyridone alkaloid, cerpegin, was synthesized in five steps starting from the Michael reaction between phenylthioacetonitrile and 2- methoxycarbonyl-4-methyl-2-penten-4-olide. Catalytic hydrogenation of a nitrile group in the presence of a conjugated
- Matsuo,Arase
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p. 2091 - 2094
(2007/10/03)
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- Synthesis of cerpegin
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Cerpegin (1), a new pyridone alkaloid, was synthesized starting from the Michael reaction of phenylthioacetonitrile (2) and 2-methoxycarbonyl-4,4- dimethyl-2-buten-4-olide (3) in five steps. Catalytic hydrogenation of a nitrile group in the presence of a
- Matsuo,Arase
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p. 715 - 717
(2007/10/02)
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