Efficient ortho-oxidation of phenol and synthesis of anti-MRSA and anti-VRE compound abietaquinone methide from dehydroabietic acid.
A quinone methide diterpene: abietaquinone methide, which possesses potent anti-methicillin-resistant Staphylococcus aureus (MRSA) and anti-vancomycin-resistant Enterococcus (VRE) activities, was synthesized via efficiently ortho-oxidation of ferruginol derived from industrially available dehydroabietic acid. ortho-Oxidation of phenols was developed to give mono esters of catechols using a stable diacyl peroxide, bis(4-chlorobenzoyl) peroxide (m-chlorobenzoyl peroxide: mCBPO) which was synthesized from meta-chlorobenzoic acid. Efficient one pot ortho-oxidation reaction of phenol with an adduct of meta-chloroperbenzoic acid (mCPBA) with dicyclohexylcarbodiimide (DCC) was also reported.
Tada
Masahiro
M
Laboratory of Bioorganic Chemistry, Tokyo University of Agriculture and Technology, Fuchu, Tokyo, Japan. tada@cc.tuat.ac.jp
Ishimaru
Kosaku
K
D045784:Abietanes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D016983:Enterococcus / Q000187:drug effects; D016106:Methicillin Resistance / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D019800:Phenol / Q000737:chemistry*; D012680:Sensitivity and Specificity; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism; D020713:Vancomycin Resistance
D045784:Abietanes; D000900:Anti-Bacterial Agents; D010616:Phenanthrenes; C516194:abietaquinone methide; C013913:dehydroabietic acid; D019800:Phenol