Practical Synthesis of (+)-Alloisoleucine
- 1 January 2000
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 30 (12) , 2245-2252
- https://doi.org/10.1080/00397910008087404
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.Keywords
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