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Enantiopure N-acyldihydropyridones as synthetic intermediates. An asymmetric synthesis of solenopsin A

✍ Scribed by Daniel L. Comins; Nezha Radi Benjelloun

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 259 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)75974-0

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✦ Synopsis

The trans-pip&dine alkaloid, (-)-solenopsin A. was prepared in seven steps from readily available 4-~haxy-3_(niiropropyrsilyllpyrfdin in 43% overall yield. The addition of organ~tallics to chiral 1-acylpyridinium salt 1 gives N-acyl-2-alkyl-23&hydta~4pyridones 2 with high diastereoselectivity.*~ The dihyedones 3. pqared from 2 in one step, am useful chiral building blocks for various alkaloids. 23 Recently, we developed a synthesis of enantiopute 2-

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