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.
Narayanan
Jayan
J
Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, MD 2089, USA.
Hayakawa
Yoshio
Y
Fan
Junfa
J
Kirk
Kenneth L
KL
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