A facile and environmentally benign KI(cat.)/NaBO·4HO oxidation system has been developed for the tandem oxidative aminocyclization/coupling of tryptamines, affording a series of 3a,3a'-bispyrrolidino[2,3-b]indolines with high efficiency (up to 94% yield). This reaction features an electrophilic "I" mechanism, which is importantly quite different from and milder than the typical radical-involving process, and can be readily amplified for the total synthesis of (+)-WIN 64821.
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