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Synthesis 2009(6): 951-956
DOI: 10.1055/s-0028-1087851
DOI: 10.1055/s-0028-1087851
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis of an (R)-Garner-type Aldehyde from l-Serine: Useful Building Block for a (+)-Furanomycin Derivative
Further Information
Received
10 November 2008
Publication Date:
02 March 2009 (online)
Publication History
Publication Date:
02 March 2009 (online)

Abstract
(+)-Furanomycin is an antibiotic that substitutes for l-isoleucine in bacterial protein translation. We propose here a new short synthesis of a useful intermediate, a 1,2-diprotected 2-aminopent-4-ene-1,3-diol, starting from the inexpensive natural amino acid l-serine, and via a Garner-type aldehyde. The (R)-α-amino aldehyde was obtained by the construction of an oxazoline ring between the N-protected amino group and the hydroxy group that resulted from reduction of the carboxylic acid functionality of l-serine.
Key words
amino acids - diastereoselectivity - lanthanides - natural products - protecting groups - Wittig reactions
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