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New synthesis of 5-amino-4-hydroxy-2,6-dimethylheptanoic acid, a hydroxyethylene isostere of the Val-Ala dipeptide

✍ Scribed by Fabio Benedetti; Paolo Maman; Stefano Norbedo

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 73 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01773-1

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✦ Synopsis

Two stereoisomers of the title compound have been synthesized from the methyl ester of N-Boc L-valine. The aminoester was initially converted into an a%-amino a,b-unsaturated ketone via a phosphonoketone and a Horner-Emmons olefination with acetaldehyde. Hydrocyanation of the enone with diethylaluminium cyanide and functional group conversions gave the hydroxyaminoacids protected as oxazolidines or as lactones.

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