The Synthesis of 3-Spirooxindole Derivatives. I. Syntheses of 1-Methyl-2', 3', 10', 10'a-tetrahydrospiro [indoline-3, 1' (5'H)-pyrrolo [1, 2-b]-isoquinoline]-2-one and its Homologs.

Abstract

The syntheses of 1-methyl-2', 3', 10', 10'a-tetrahydrospiro [indoline-3, 1'(5'H)-pyrrolo-[1, 2-b]isoquinoline]-2-one (XIII) and its homologs were described. The compound XIII was identified with the dehydrogenation product of 1-methyl-2-hydroxy-3-[2-(1, 2, 3, 4-tetrahydro-2-isoquinolyl) ethyl] indole (XV), which established Belleau's assignment to the key intermediate in Julian's synthesis of the yohimbine ring system.