First synthesis of N-(3-carboxylpropyl)-5-amino-2-hydroxy-3- tridecyl-1,4-benzoquinone, an unusual quinone isolated from Embelia ribes.
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.
McErlean
Christopher S P
CS
School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, United Kingdom.
Moody
Christopher J
CJ
D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D031645:Embelia / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D016227:Benzoquinones; C527465:N-(3-carboxylpropyl)-5-amino-2-hydroxy-3-tridecyl-1,4-benzoquinone; D005680:gamma-Aminobutyric Acid