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2886110 
Journal Article 
Efficient ortho-oxidation of phenol and synthesis of anti-MRSA and anti-VRE compound abietaquinone methide from dehydroabietic acid 
Tada, M; Ishimaru, K 
2006 
Yes 
Chemical and Pharmaceutical Bulletin
ISSN: 0009-2363
EISSN: 1347-5223 
54 
10 
1412-1417 
English 
17015979 
WOS:000241549300010 
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. 
anti-methicillin-resistant bacteria; quinone methide; m-chlorobenzoyl peroxide; ortho-oxidation; anti-methicillin-resistant Staphylococcus aureus (MRSA); anti-vancomycin-resistant Enterococcus (VRE)