Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 27, Pages 8288-8292Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201402175
Keywords
aminoglycoside; azidization; conduramines; palladium; synthetic methods
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Funding
- NIH-GM
- National Science Foundation
- Eli Lilly
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1145236] Funding Source: National Science Foundation
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A concise asymmetric synthesis of aminocyclitols, such as diastereomeric 2-deoxystreptamine analogues and conduramine A, is described. The Pd-catalyzed asymmetric desymmetrization of meso 1,4-dibenzolate enables the synthesis of highly oxidized cyclohexane architectures. These scaffolds can potentially be used to access new aminoglycoside antibiotics and enantiomerically pure alpha-glucosidase inhibitors.
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