Concise and enantioselective synthesis of the aminocyclitol core of hygromycin A.
[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%).
Donohoe
Timothy J
TJ
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk
Johnson
Peter D
PD
Pye
Richard J
RJ
Keenan
Martine
M
D002934:Cinnamates / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D006921:Hygromycin B / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007294:Inositol / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D002934:Cinnamates; D006921:Hygromycin B; C026273:hygromycin A; D007294:Inositol