Stereocontrolled Addition of 2-Thiazolyl Organometallic Reagents toC-Galactopyranosylnitrone. A Formal Synthesis of Destomic Acid and Lincosamine
- 1 January 1993
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1993 (01) , 78-80
- https://doi.org/10.1055/s-1993-22356
Abstract
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.Keywords
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