Synthesis of the glucoallosamidin pseudo-disaccharide: Use of an efficient Hg(II) mediated cyclization

Add time:08/29/2019    Source:sciencedirect.com

The title compound 1a was prepared from cyclopentadienylthallium in 11 steps. The key component of the pseudo-disaccharide 1a, (−)-allosamizoline 2, was synthesized in 2 steps starting from the known cyclopentene 4 by formation of the aminoimidate 5 followed by a mercury(II)trifluoroacetate mediated cyclization and radical oxygenation. Regioselective and stereospecific coupling of 6-O-benzyl-(−)-allosamizoline8 with the oxazoline glycosyl donor 11 and subsequent deprotection afforded the β-1,4-pseudo-disaccharide 1a.

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