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Synthesis 2009(6): 951-956  
DOI: 10.1055/s-0028-1087851
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of an (R)-Garner-type Aldehyde from l-Serine: Useful Building Block for a (+)-Furanomycin Derivative

Giuseppe Bartolia, Giustino Di Antoniob, Roberto Fiocchic, Sandra Giuli*c, Enrico Marcantoni*c, Mauro Marcolinic
a Department of Organic Chemistry ‘A. Mangini’, University of Bologna, Viale Risorgimento 4, 40136 Bologna, Italy
b Chemistry Research Centre, Boehringer-Ingelheim S.p.A., via Lorenzini 8, 20139 Milano, Italy
c Department of Chemical Sciences, University of Camerino, via S. Agostino 1, 62032 Camerino (MC), Italy
Fax: +39(737)402297; e-Mail: enrico.marcantoni@unicam.it;
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Received 10 November 2008
Publikationsdatum:
02. März 2009 (online)

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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