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De Novo Synthesis of the Trisaccharide Subunit of Landomycins A and E

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journal contribution
posted on 2008-06-05, 00:00 authored by Maoquan Zhou, George A. O’Doherty
A highly enantio- and diastereoselective synthesis of α-l-rhodinose, β-d-olivose as well as the trisaccharide portion of landomycin A from achiral acetyl furan has been developed. The key transformations include the palladium-catalyzed glycosylation, Myers’ reductive rearrangement, diastereoselective dihydroxylation, and regioselective Mitsunobu inversion. A Mitsunobu reaction on a six member ring cis-1,2-diol was found to chemoselectively discriminate between equatorial and axial alcohols and to stereoselectively convert cis-1,2-diol into anti-1,2-diol.

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