Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Efficient ortho-Oxidation of Phenol and Synthesis of Anti-MRSA and Anti-VRE Compound Abietaquinone Methide from Dehydroabietic Acid
Masahiro TadaKosaku Ishimaru
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2006 Volume 54 Issue 10 Pages 1412-1417

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Abstract

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.

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© 2006 The Pharmaceutical Society of Japan
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