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Construction of the Azacyclic Core of Tabernaemontanine-Related Alkaloids via Tandem Reformatsky-Aza-Claisen Rearrangement.

Young-Ger Suh, Changjin Lim, Jaehoon Sim, Jae Kyun Lee, Young-Joon Surh, Seung-Mann Paek
Journal of Organic Chemistry 2017 Februrary 4
A divergent synthetic methodology for a tabernaemontanine-related alkaloid was developed. The synthetic route features practical improvements in the Pictet-Spengler cyclization for the tetrahydro-β-carboline intermediate and an unprecedented tandem Reformatsky-aza-Claisen rearrangement to create the core carbon skeleton and stereochemistries of tabernaemontanine-related alkaloids.

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