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Initial attemps in order to deprotect the amino group at N-10 before the manipulation of the functional groups, forced us to carry out this operation just before the lactam formation. 1) the hydrolysis of the remaining Phac group, present in D-12 and 20, in the same enzymatic reaction but with longer reaction time, gave only unreacted starting material. The same result was observed at pH 11. For related hydrolyses, see: G. Cardillo, A. Tolomilli, C. Tomasini, J. Org. Chem. 1996, 61, 8651-8654; 2) the hydrolysis of the two protecting groups present in 20 using HCl at reflux gave the respective diamino indole which we were not able to monoprotect.
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1H NMR, HRMS) with the ones of 32/2 showed conclusive evidence of the modification of the triple bond during the solid-phase sequence.
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Kazanietz, M.G.1
Areces, L.B.2
Bahador, A.3
Mischak, H.4
Goodnight, J.5
Mushinski, J.F.6
Blumberg, P.7
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