Application Of Sequential Proline-Catalyzed Alpha-Chlorination And Aldol Reactions In The Total Synthesis Of 1-Deoxygalactonojirimycin
CANADIAN JOURNAL OF CHEMISTRY(2018)
Abstract
A short enantioselective total synthesis of 1-deoxygalactonojirimycin (migalastat) has been achieved that does not rely on chiral pool starting materials or biocatalysis. Instead, this synthesis exploits a one-pot proline-catalyzed alpha-chlorination and aldol reaction of a commercially available aldehyde to assemble the entire carbon skeleton in a single step. The key role played by a nitrogen protecting group in the final epoxide opening reaction is highlighted as is the amenability to access structural analogues using this route.
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Key words
1-deoxygalactonojirimycin, iminosugar, organocatalysis, chlorohydrin, total synthesis, natural product
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