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[reaction: see text] Stereoselective aminohydroxylation and dihydroxylation using osmium(VIII) oxidants enabled the short and efficient synthesis of the aminocyclitol core of hygromycin A. In addition to allowing the selective introduction of the heteroatoms N and O, the use of osmium (via an osmate ester) as a protecting group for a 1,2-glycol is also reported. This tactic allowed efficient differentiation of otherwise equivalent hydroxyl groups and allowed us to complete the synthesis in short order (14 steps) and excellent overall yield (12%).

Original publication

DOI

10.1021/ol0473750

Type

Journal article

Journal

Org Lett

Publication Date

31/03/2005

Volume

7

Pages

1275 - 1277

Keywords

Cinnamates, Crystallography, X-Ray, Hygromycin B, Inositol, Molecular Structure, Stereoisomerism, Streptomyces