Outlined herein is a novel and scalable synthesis of (-)-vindorosine based on two key transformations. A highly diastereoselective vinylogous Mannich addition of dioxinone-derived lithium dienolates with indolyl N-tert-butanesulfinyl imines has been developed. In addition, an intramolecular Heathcock/aza-Prins cyclization was introduced to construct both the C, and the highly substituted E rings for the synthesis of (-)-vindorosine and related alkaloids.
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Chen et al. (2017) studied this question.
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