Practical Synthesis of (+)-Alloisoleucine |
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| Authors: | Czeslaw Belzecki Jerzy Trojnar Marek Chmielewski |
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| Affiliation: | 1. Institute of Organic Chemistry of the Polish Academy of Sciences , 01–224, Warsaw, Poland;2. Ferring Research Institute Inc , San Diego, CA, 92121, USA |
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| Abstract: | Subsequent treatment of N-crotoyl-(1S,2R)-bornane-10,2-sultam with EtMgCl, recrystallization of the product and saponification, afforded R-(-)-3-methylpenthanoic acid which was used for acylation of (1R,2S)-bornane-10,2-sultam. The product was converted into N-(2S,3R)-2-amino-3-methylpentanoyl]-(1R,2S)-bornane-10,2-sultam by hydroxyamination with 1-chloro-1-nitrosocyclohexane, followed by reduction of the hydroxylamine grouping. Saponification of the sultam imide provided (+)-alloisoleucine. |
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| Keywords: | Styryl dyes Microwave irradiation Ac2O Benzimidazole nucleus |
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