Totally chemical synthesis of azasugars via thiazole intermediates. Stereodivergent routes to (-)-nojirimycin, (-)-mannojirimycin and their 3-deoxy derivatives from serine
The synthesis of the (-)-antipodes of the natural products nojirimycin (+)-1 and mannojirimycin (+)-2 has been carried out by stereocontrolled reduction of the thiazole ketone 7 as a common key intermediate. This ketone was in turn obtained from the L-serine derived aldehyde 3 by two convergent routes involving carbonylolefination and dihydroxylation processes. Moreover, 3-deoxy derivatives of (-)-1 and (-)-2 have been prepared from 3 and the lithium enolate of 2-acetylthiazole followed by stereocontrolled reduction of the resultant aldol.
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