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Updated: Nov 2, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthetic studies toward longeracemine: a SmI2-mediated spirocyclization and rearrangement cascade to construct the
Keita Komine1, Kyle M Lambert1, Quentin R Savage1
1Department of Chemistry and Biochemistry, Baylor University One Bear Place 97348 Waco TX 76798 USA john_l_wood@baylor.edu.
Abstract:
Longeracemine, a member of the Daphniphyllum family of alkaloids contains a novel carbon framework featuring a highly functionalized 2-azabicyclo[2.2.1]heptane core as part of an overall 5/6/5/5/6/5 skeleton. A synthetic intermediate containing the core of longeracemine has been efficiently prepared by employing a stereoselective SmI2-mediated cascade reaction to advance a 7-azabicyclo[2.2.1]heptadiene to a 2-azabicyclo[2.2.1]heptene that is functionally poised for conversion to the natural product.
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