1965
DOI: 10.1016/s1876-0813(08)60051-2
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Chapter 12 The Vinca Alkaloids

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“…47,48 Thus, the formation of both products can be rationalized considering an initial formation of indolenyl hydroperoxide 4a, which can be reduced to the corresponding 7-hydroxyindolenine 5a (a transformation that can occur spontaneously in the reaction medium) 49 or further rearranged to the keto lactam 6 via a dioxetane intermediate (for a possible mechanism see Figure 2). 50 Although previous work indicated the feasibility of isolation of the indolenyl hydroperoxide 4a, 35,34 we could not isolate it under these conditions, probably because of its rapid decomposition during the purification process. Thus, ibogaine, but not voacangine, reacts with dioxygen in a fundamental state in toluene, probably through a radical mechanism (intermediate A, Figure 2).…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…47,48 Thus, the formation of both products can be rationalized considering an initial formation of indolenyl hydroperoxide 4a, which can be reduced to the corresponding 7-hydroxyindolenine 5a (a transformation that can occur spontaneously in the reaction medium) 49 or further rearranged to the keto lactam 6 via a dioxetane intermediate (for a possible mechanism see Figure 2). 50 Although previous work indicated the feasibility of isolation of the indolenyl hydroperoxide 4a, 35,34 we could not isolate it under these conditions, probably because of its rapid decomposition during the purification process. Thus, ibogaine, but not voacangine, reacts with dioxygen in a fundamental state in toluene, probably through a radical mechanism (intermediate A, Figure 2).…”
Section: ■ Results and Discussionmentioning
confidence: 99%