Diastereospecific synthesis of ketooxindoles. Potential intermediates for the synthesis of alstonisine as well as for Voachalotine related oxindole alkaloids
A convenient method has been developed to convert N-a-H tetracyclicketone Ia into the two corresponding oxindoles[C(7)] diastereospecifically. Treatment of the N-a-H, N-b-benzyl tetracyclicketone la with t-BuOCl provided diastereomer 2a (related to Voacanga oxindoles), whereas the same process with N-b-H (Ib) or N-b-benzoyl (Ic) substituted analogs funished the diastereomers 2b and 2c (related to alstonisine), respectively. (C) 1997 Elsevier Science Ltd.