Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 5, Pages 1935-1940Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo702476q
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- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0749451, 1114891] Funding Source: National Science Foundation
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[GRAPHICS] An enantioselective and diastereocontrolled approach to 8a-epi-D-swainsonine has been developed from achiral furfural. The key step to this synthesis was a one-pot procedure for the hydrogenolytic removal of two protecting groups and two intramolecular reductive amination reactions. The absolute stereochemistry was introduced by asymmetric Noyori reduction of furfuryl ketone. This route relies on diastereoselective palladium-catalyzed glycosylation to install the anomeric bond, and Luche reduction, diastereoselective dihydroxylation to set up the manno-stereochemistry of the indolizidine precursor.
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