The Journal of organic chemistry

First synthesis of N-(3-carboxylpropyl)-5-amino-2-hydroxy-3-tridecyl-1, 4-benzoquinone, an unusual quinone isolated from Embelia ribes

CSP McErlean, CJ Moody

Index: McErlean, Christopher S. P.; Moody, Christopher J. Journal of Organic Chemistry, 2007 , vol. 72, # 26 p. 10298 - 10301

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Citation Number: 27

Abstract

The first synthesis of the unusual nitrogen-containing 3-alkyl-1, 4-benzoquinone, N-(3- carboxylpropyl)-5-amino-2-hydroxy-3-tridecyl-1, 4-benzoquinone, isolated from Embelia ribes, is reported. The key steps are a microwave-assisted combined Mitsunobu reaction- Claisen rearrangement to introduce the alkyl side chain into 2, 5-dimethoxyphenol, followed by alkene reduction, oxidation to the quinone, and sequential displacement of the ...