Abstract
The enzyme inhibitor RK-682 (5R)-(+)-1 was prepared in solution and on a solid support from (2R)-glycerates in five steps and ca. 40% overall yield. Key steps were a ring-closing tandem addition-Wittig alkenation reaction of the respective protected or immobilized glycerates with the ylide Ph(3)PCCO and the 3-acylation of the tetronic acids thus obtained with palmitic acid. A similar route extended by a mesylation-elimination sequence led to antibiotic agglomerins A-C 2 featuring 3-acyl-5-methylidenetetronic acid structures.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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4-Butyrolactone / analogs & derivatives
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Acylation
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Anti-Bacterial Agents / chemical synthesis*
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Enzyme Inhibitors / chemical synthesis*
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Furans / chemistry
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Glyceric Acids / chemistry
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Molecular Structure
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Palmitic Acid / chemistry
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Phosphoprotein Phosphatases / antagonists & inhibitors*
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Phosphoprotein Phosphatases / chemical synthesis
Substances
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Anti-Bacterial Agents
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Enzyme Inhibitors
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Furans
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Glyceric Acids
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RK 682
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agglomerin A
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agglomerin B
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agglomerin C
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Palmitic Acid
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glyceric acid
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Phosphoprotein Phosphatases
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tetronic acid
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4-Butyrolactone