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© 2014 Elsevier Ltd. Abstract Diastereoselective syn- and anti-dihydroxylations of enantiopure tetrahydropyridine and tetrahydroazepine scaffolds have been used in total asymmetric syntheses of the polyhydroxylated azacycles (-)-fagomine, (-)-3-epi-fagomine, (-)-5-epi-fagomine and two related polyhydroxylated azepanes. In each case, the target compounds were isolated as single diastereoisomers (>99:1 dr) in fewer than eight steps from the commercially available starting materials, sorbic acid and the requisite α-methylbenzylamine.

Original publication

DOI

10.1016/j.tet.2014.12.004

Type

Journal article

Journal

Tetrahedron

Publication Date

17/08/2015

Volume

71

Pages

7170 - 7180