(±)-3'-Deoxyaraaristeromycin via a surprising rearrangement
Hydrolysis of (±)-3β-acetoxy-4α-benzamido-1α-cyclopentanemethyl acetate (5) with 6 N hydrochloric acid has been found to give an amine in which the configuration at C-3 has been inverted. This conclusion was reached following conversion of the amine into (±)-3'-deoxyaraaristeromycin (8) by following a standard adenine formation process of (i) reaction with 5-amino-4,6-dichloropyrimidine, (ii) ring closure with diethoxymethyl acetate, and (iii) ammonolysis. Use of basic hydrolysis conditions with 5 led to the expected (±)-3'-deoxyaristeromycin (7).
Frick,Patil,Gambino,Schneller
p. 5541 - 5544
(2007/10/02)
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