Abstract
(16S)-Preakuammicine has been considered a key intermediate in the biosynthesis of monoterpene indole alkaloids since the 1970s. Indeed, preakuammicine plays a crucial role in the biosynthesis of type II and type III monoterpene indole alkaloids and strychnine. In this paper, we disclose the unprecedented biomimetic transformation of akuammiline into (16R)-acetylpreakuammicine, which ultimately gives mechanistic insight into a missing step in biosynthetic pathways. This work affords the first spectroscopic data for this never-described framework. The C16 stereochemistry of preakuammicine involved in the biosynthesis of akuammicine is reassigned and leads to the consideration of both the (16R) and the (16S) diastereomers of preakuammicine as biosynthetic intermediates.
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