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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

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Christopher S. P. McErlean and Christopher J. Moody*

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

J. Org. Chem., 2007, 72 (26), pp 10298–10301

DOI: 10.1021/jo702101w

Publication Date (Web): November 14, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

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

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Published In Issue December 21, 2007
Received September 26, 2007

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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

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SciFinder Links

History

Recommend & Share

Related Content

Stereoselective Total Syntheses of Three Lycopodium Alkaloids, (−)-Magellanine, (+)-Magellaninone, and (+)-Paniculatine, Based on Two Pauson−Khand Reactions

Studies toward the Total Synthesis of Nominine

Development of a Highly β-Selective Ribosylation Reaction without Using Neighboring Group Participation: Total Synthesis of (+)-Caprazol, a Core Structure of Caprazamycins

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