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ChemInform Abstract: Radical Cyclizations of 1,4-Dihydropyridines. Synthesis of Chiral Fused Nitrogen Heterocycles. Synthesis of Lupinine and Epilupinine.

✍ Scribed by P. MANGENEY; L. HAMON; S. RAUSSOU; N. URBAIN; A. ALEXAKIS

Publisher
John Wiley and Sons
Year
2010
Weight
42 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Radical Cyclizations of 1,4-Dihydropyridines. Synthesis of Chiral Fused Nitrogen Heterocycles. Synthesis of Lupinine and Epilupinine.

-A detailed investigation of radical cyclizations of chiral 1,4-dihydropyridines under different reaction conditions is presented. The presence of an aldehyde group at C3 of the dihydropyridine is found to be crucial for the diastereoselectivity of the anellation reaction. Best results are obtained using ultrasonic conditions according to Luches protocol. Based on this study, syntheses of the lupin alkaloids lupinine (XX) and epilupinine (XXII) are achieved.

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