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The asymmetric synthesis of (2S,3R)-capreomycidine

✍ Scribed by Duane E DeMong; Robert M Williams

Book ID: 104230555
Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 67 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00487-7

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✦ Synopsis

An improved asymmetric synthesis of the guanidine-containing amino acid (2S,3R)-capreomycidine has been achieved in seven steps and 28% overall yield. The key synthetic step involved a Mannich-type reaction between a chiral glycine aluminum enolate and the benzyl-imine of 3-tert-butyldimethylsiloxy-propionaldehyde.

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