Abstract
Two different strategies leading to formal total syntheses of platencin are described. The first strategy involving Claisen rearrangement and radical cyclization provides a rapid access to the core structure of platencin, and also use minimum protective-group operations. The second strategy, a protecting group-free route, utilizes a 6-exo-trig radical cyclization and aldol condensation as key steps leading to the formal synthesis of platencin.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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3-Oxoacyl-(Acyl-Carrier-Protein) Synthase
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Acetyltransferases / antagonists & inhibitors*
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Acetyltransferases / metabolism
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Aminophenols / analysis
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Aminophenols / chemical synthesis*
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Aminophenols / pharmacology
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Anti-Bacterial Agents / analysis
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Anti-Bacterial Agents / chemical synthesis*
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Anti-Bacterial Agents / pharmacology
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Bacteria / drug effects
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Bacteria / enzymology
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Bacterial Infections / drug therapy
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Bacterial Infections / microbiology
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Chemistry, Pharmaceutical / methods*
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Cyclization
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Drug Discovery
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Escherichia coli Proteins / antagonists & inhibitors*
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Escherichia coli Proteins / metabolism
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Fatty Acid Synthase, Type II / antagonists & inhibitors
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Fatty Acid Synthase, Type II / metabolism
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Fatty Acids / metabolism
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Free Radicals / chemistry
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Humans
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Lipid Metabolism / drug effects
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Molecular Structure
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Polycyclic Compounds / analysis
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Polycyclic Compounds / chemical synthesis*
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Polycyclic Compounds / pharmacology
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Stereoisomerism
Substances
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Aminophenols
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Anti-Bacterial Agents
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Escherichia coli Proteins
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Fatty Acids
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Free Radicals
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Polycyclic Compounds
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Acetyltransferases
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fabH protein, E coli
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3-Oxoacyl-(Acyl-Carrier-Protein) Synthase
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Fatty Acid Synthase, Type II
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platencin