First Synthesis of N-(3-Carboxylpropyl)-5-amino-2-hydroxy-3- tridecyl-1,4-benzoquinone, an Unusual Quinone Isolated from Embelia ribes.

First Synthesis of N-(3-Carboxylpropyl)-5-amino-2-hydroxy-3- tridecyl-1,4-benzoquinone, an Unusual Quinone Isolated from Embelia ribes. Research Abstract Details 

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First Synthesis of N-(3-Carboxylpropyl)-5-amino-2-hydroxy-3- tridecyl-1,4-benzoquinone, an Unusual Quinone Isolated from Embelia ribes. Abstract Text:

Christopher S P McErlean,Christopher J Moody,Christopher S P McErlean,Christopher J Moody,Christopher S P McErlean,Christopher J Moody,

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 methoxy groups with hydroxide and GABA tert-butyl ester. Two other naturally occurring benzoquinones, O-methylrapanone and rapanone, were also prepared en route.

First Synthesis of N-(3-Carboxylpropyl)-5-amino-2-hydroxy-3- tridecyl-1,4-benzoquinone, an Unusual Quinone Isolated from Embelia ribes. Publishing Authors By Initials

CS McErlean,CJ Moody,CS McErlean,CJ Moody,CS McErlean,CJ Moody,

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First Synthesis of N-(3-Carboxylpropyl)-5-amino-2-hydroxy-3- tridecyl-1,4-benzoquinone, an Unusual Quinone Isolated from Embelia ribes. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: The Journal of organic chemistry

VOLUME: 72

Page Numbers: 10298-301

Journal Abbreviation: J. Org. Chem.

ISSN: 0022-3263

DAY: 14

MONTH: 11

YEAR: 2007

First Synthesis of N-(3-Carboxylpropyl)-5-amino-2-hydroxy-3- tridecyl-1,4-benzoquinone, an Unusual Quinone Isolated from Embelia ribes. Information

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LANGUAGE: eng

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AFFILIATION: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, United Kingdom c.j.moody@nottingham.ac.uk.

Country: United States

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MEDLINETA: J Org Chem

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