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Synlett 1997; 1997(1): 83-84
DOI: 10.1055/s-1997-696
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Asymmetric Synthesis of D-Fucosamine and N-Methyl-D-Fucosamine

Vicente Ojea, María Ruiz, José M. Quintela*
  • *Departamento de Química Fundamental e Industrial. Universidade de Coruña. Campus A Zapateira s/n, La Coruña E-15071, Spain, Fax 34 81 135641; E-mail jqqoqf@udc.es
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Publication Date:
22 March 2004 (online)

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(+)-D-fucosamine and (+)-N-methyl-D-fucosamine (the amino sugar moiety of neocarzinostatin) have been synthesized from known building blocks derived from natural amino acids. Direct and diastereoselective construction of the key intermediate 4 was accomplished by a syn-aldol type reaction between Schöllkopf's bislactim ether 2 and the 1,3-dioxolane-4-carboxaldehyde 3. Reduction and monomethylation of a O'Donnell's Schiff base derived from the common amino ester 7 allows an optional access to the N-methyl derivative.

2-amino-2,6-dideoxy-galactose - neocarzinostatin - amino acid based synthesis - syn-aldol addition