Convenient syntheses of biogenic aldehydes, 3,4-dihydroxyphenylacetaldehyde and 3,4-dihydroxyphenylglycolaldehyde.
The title compounds were prepared from a common precursor, a bis-THP-protected dihydroxyphenylacetic acid methyl ester. Key steps are the introduction of the alpha-hydroxyl group by Davis oxaziridine reagent and formation of the aldehydes by DIBALH ester reduction.
Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, MD 2089, USA.
Jayan
J
Narayanan
Yoshio
Y
Hayakawa
Junfa
J
Fan
Kenneth L
KL
Kirk
D015102:3,4-Dihydroxyphenylacetic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D002396:Catechols; D006868:Hydrolysis; D017665:Hydroxyl Radical / Q000737:chemistry; D007202:Indicators and Reagents
D000447:Aldehydes; D002396:Catechols; D007202:Indicators and Reagents; D015102:3,4-Dihydroxyphenylacetic Acid; C007431:3,4-dihydroxyphenylglycolaldehyde; D017665:Hydroxyl Radical; C007430:3,4-dihydroxyphenylacetaldehyde