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

J Org Chem

College of Pharmacy, Research Institute of Pharmaceutical Science, Gyeongsang National University, Jinju daero, Jinju 660-751, Republic of Korea.

Published: February 2017

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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http://dx.doi.org/10.1021/acs.joc.6b02648DOI Listing

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