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Synthesis of 1‐(β‐D‐ribofuranosyl)indol‐3‐acetic acid
Author(s) -
Chu Chung K.,
Suh Jungjin,
Cutler Horace G.
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230635
Subject(s) - chemistry , acetic acid , methanol , indoline , yield (engineering) , ethyl acetate , nucleoside , organic chemistry , condensation , phosphoric acid , medicinal chemistry , stereochemistry , materials science , physics , metallurgy , thermodynamics
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 ).