Popik, O.; Pasternak-Suder, M.; Baś, S.; Mlynarski, J.
Organocatalytic Synthesis of Higher-carbon Sugars: Efficient Protocols for the Synthesis of Natural Seduheptulose and D-glycero-L-galacto-oct-2-ulose
ChemistryOpen 2015 (link to page)
We report short and efficient protocol for the synthesis of naturally occurring higher-carbon seduheptulose (D-altro-hept-2-ulose) and D-glycero-L-galacto-oct-2-ulose, from the readily available sugar aldehydes and dihydroxyacetone (DHA). The key step includes diastereoselective organocatalytic syn-selective aldol reaction of DHA with D-erythrose and D-xylose, respectively.
Popik, O.; Zambroń, B.; Mlynarski, J.
Biomimetic syn-Aldol Reaction of Dihydroxyacetone Promoted by Water-Compatible Catalysts
Eur. J. Org. Chem.2013 7484-7487 (link to page)
syn-Selective direct aldol reaction of unprotected dihydroxyacetone (DHA) with D- or L-glyceraldehyde catalyzed by serine-based organocatalysts leads to D- or L- configured fructose and sorbose with excellent diasteroselectivity (up to 95:5 dr).
Nicolas, C.; Pluta, R.; Pasternak-Suder, M.; Martin, O. R.; Mlynarski, J.
Organocatalytic syn-Aldol Reactions of Hydroxyacetone with (S)-Isoserinal Hydrate: Asymmetric Synthesis of 1,5,6-Trideoxy-1,5-imino-L-mannitol and 1,5,6-Trideoxy-1,5-imino-D-glucitol
Eur. J. Org. Chem. 2013 1296-1305 (link to page)
A novel and original protocol for the preparation of 1,5,6-trideoxy-1,5-imino-L-mannitol and 1,5,6-trideoxy-1,5-imino-D-glucitol is reported. The key steps includes organocatalyzed syn selective direct aldol reaction of hydroxyacetone and CBz-protected isoserinal hydrate followed by reductive amination/ cyclization.