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11:45
Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
A piperidine chiron for the Veratrum alkaloids
Douglass F Taber1, Peter W DeMatteo
1Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
The Journal of Organic Chemistry
|March 10, 2012
Summary
A novel Veratrum piperidine chiron was synthesized in 11 steps from (-)-citronellal. This study presents three methods for adding a propargylic side chain to a cyclic enamide, advancing synthetic organic chemistry.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Chirons are valuable chiral building blocks in organic synthesis.
- Developing efficient synthetic routes to complex molecules is crucial.
Purpose of the Study:
- To synthesize a Veratrum piperidine chiron.
- To explore and present methods for propargylic side chain installation onto cyclic enamides.
Main Methods:
- Multi-step synthesis starting from (-)-citronellal.
- Utilized three distinct methodologies for propargylic group attachment.
- Characterization of the synthesized Veratrum piperidine chiron.
Main Results:
- Successful synthesis of the Veratrum piperidine chiron in 11 steps.
- Achieved an overall yield of 7.9% for the synthetic route.
- Demonstrated the efficacy of three different methods for propargylic side chain installation.
Conclusions:
- The presented synthetic route provides a viable pathway to the Veratrum piperidine chiron.
- The developed methods for propargylic side chain installation offer versatile tools for organic synthesis.
- This work contributes to the advancement of chiral synthesis and methodology development.
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