Article

Synthesis of 1‐(β‐D‐ribofuranosyl)indol‐3‐acetic acid

Journal of Heterocyclic Chemistry (Impact Factor: 1.22). 03/2009; 23(6):1777 - 1779. DOI: 10.1002/jhet.5570230635

ABSTRACT By condensation of ethyl indolin-3-acetate (4) and 2,3,5-tri-O-benzoylribofuranosyl-1-acetate (5), ethyl 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)indolin-3-acetate (6) was obtained in good yield. The indoline nucleoside 6 was aromatized to ethyl 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)indol-3-acetate (7) with DDQ. The treatment of the indole nucleoside with barium hydroxide and methanol gave the methyl ester 8, which was further treated in water to give the desired 1-(β-D-ribofuranosyl)indol-3-acetic acid (9).

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