Synthetic Communications p. 2245 - 2252 (2000)
Update date:2022-08-17
Topics:
Belzecki, Czeslaw
Trojnar, Jerzy
Chmielewski, Marek
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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