Diastereoselective concise syntheses of the polyhydroxylated alkaloids DMDP and DAB |
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Authors: | Marc E Bouillon Stephen G Pyne |
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Institution: | School of Chemistry, University of Wollongong, Wollongong, New South Wales 2522, Australia |
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Abstract: | A diastereoselective concise synthesis of the iminosugars DMDP and DAB is presented starting from l-xylose and affording the two alkaloids in good yields of 35% and 22% over seven and eight steps, respectively. The Petasis borono–Mannich reaction of 3,5-di-O-benzyl-l-xylofuranose with benzylamine and (E)-styrylboronic acid served as the nitrogen-introducing key step furnishing the new C–N bond in an entirely diastereoselective manner. A chemo- and regioselective O-mesylation followed by an intramolecular SN2-cyclisation allowed the formation of the pyrrolidine ring. Ozonolysis of the styryl double bond and subsequent reduction to form the C-5 hydroxymethyl substituent followed by hydrogenolysis of the benzyl protecting groups concluded the DMDP synthesis. Furthermore, an unexpected fragmentation process during the ozonolysis reaction also gave access to the C-5 decarbinolated DMDP derivative DAB. |
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Keywords: | CRYZWIGCKOYGLJ-RXUBUJBPSA-N HIZKDEYTZOKLDR-TWJOJJKGSA-N JNCQINMEVPHWGU-LKWPHFQBSA-N XINQELFVOYWANL-YFRBGRBWSA-N DNINTJBHUBQIAM-CRJNBBPJSA-N NPNKRWIUUXWYLW-FPCALVHFSA-N JLCCWJSEJJNTRQ-OXGMKNIMSA-N ZKUMYXIOGIJPLS-KZXKDKCNSA-N ISHUCMLMSAKTDK-GKCPCVQXSA-N |
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