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Synthesis of 5‐ epi ‐Isofagomine via Asymmetric Chelate–Enolate Claisen Rearrangement
Author(s) -
Schneider Christiane,
Kazmaier Uli
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199806)1998:6<1155::aid-ejoc1155>3.0.co;2-g
Subject(s) - chemistry , claisen rearrangement , stereochemistry , stereoselectivity , glycoside hydrolase , chelation , organic chemistry , enzyme , catalysis
Polyhydroxylated piperidines are an interesting class of glycosidase inhibitors. Chelate enolate Claisen rearrangement of N ‐protected chiral amino acid esters gives rise to γ,δ‐unsaturated amino acids, which can be converted to this type of alkaloids. The potential glycosidase inhibitor 5‐ epi ‐isofagomine ( 5 ) was synthesized by this approach in a highly stereoselective fashion.