Journal
NATURE CHEMISTRY
Volume 9, Issue 12, Pages 1213-1221Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.2835
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Funding
- NIH [GM-55382, SIG S10-RR027172]
- Berkeley Center for Green Chemistry Systems Approach to Green Energy Integrated Graduate Education and Research Traineeship
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Polyoxygenated hydrocarbons that bear one or more hydroxyl groups comprise a large set of natural and synthetic compounds, often with potent biological activity. In synthetic chemistry, alcohols are important precursors to carbonyl groups, which then can be converted into a wide range of oxygen- or nitrogen-based functionality. Therefore, the selective conversion of a single hydroxyl group in natural products into a ketone would enable the selective introduction of unnatural functionality. However, the methods known to convert a simple alcohol, or even an alcohol in a molecule that contains multiple protected functional groups, are not suitable for selective reactions of complex polyol structures. We present a new ruthenium catalyst with a unique efficacy for the selective oxidation of a single hydroxyl group among many in unprotected polyol natural products. This oxidation enables the introduction of nitrogen-based functional groups into such structures that lack nitrogen atoms and enables a selective alcohol epimerization by stepwise or reversible oxidation and reduction.
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