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Synlett 1993; 1993(1): 78-80
DOI: 10.1055/s-1993-22356
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Stereocontrolled Addition of 2-Thiazolyl Organometallic Reagents to C-Galactopyranosylnitrone. A Formal Synthesis of Destomic Acid and Lincosamine

Alessandro Dondoni* , Santiago Franco, Francisco Merchan, Pedro Merino, Tomas Tejero
  • *Dipartimento di Chimica, Iaboratorio di Chimica Organica, Università, Ferrara, Italy
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Publication Date:
19 March 2002 (online)

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A complementary diastereofacial selectivity is achieved in the addition of 2-lithiothiazole 1b to precomplexed C-galactopyranosyl nitrone 5 with MgBr2- or ZnCl2 and Et2AlCl or TiCl4, giving rise after the thiazole-to-aldehyde unmasking, to the epimeric amino-dialdoses 9 and 15, advanced intermediates in syntheses of destomic acid and lincosamine respectively. A similar result is obtained by using 2-thiazolylmagnesium bromide 1c and 2-diethylaluminum)thiazole 1d in the presence of the above Lewis acids.