Practical synthesis of (+)-alloisoleucine

Article abstract of DOI:10.1080/00397910008087404

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.

Full text of DOI:10.1080/00397910008087404

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Synthetic Communications: An
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Practical Synthesis of (+)-
Alloisoleucine
a
b
Czeslaw Belzecki , Jerzy Trojnar & Marek
a
Chmielewski
a
Institute of Organic Chemistry of the Polish
Academy of Sciences, 01–224, Warsaw, Poland
b
Ferring Research Institute Inc, San Diego, CA,
92121, USA
Version of record first published: 04 Dec 2007.
To cite this article: Czeslaw Belzecki , Jerzy Trojnar & Marek Chmielewski (2000):
Practical Synthesis of (+)-Alloisoleucine, Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 30:12, 2245-2252
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