Concise and enantioselective synthesis of the aminocyclitol core of hygromycin A
| Autor: | Richard J. Pye, Timothy J. Donohoe, Martine Keenan, Peter D. Johnson |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
Molecular Structure
Stereochemistry Organic Chemistry Enantioselective synthesis chemistry.chemical_element Stereoisomerism Crystallography X-Ray Biochemistry Streptomyces Aminocyclitol chemistry.chemical_compound chemistry Cinnamates Dihydroxylation Stereoselectivity Osmium Hygromycin B Physical and Theoretical Chemistry Protecting group Inositol |
| Popis: | [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%). |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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