Synthesis of a Model Compound of Corydendramine A via a Julia Coupling

Abstract

The synthesis of the tetraenylpiperidine 12, which has the same core structure as the natural product corydendramine A, has been completed in eight steps starting from 2-piperidinemethanol 3 and trans,trans-2,6-nonadienal 6. The key step of the synthesis was a Julia coupling of sulfone (10) with aldehyde (5) to form a conjugated triene.

Keywords:

• Julia coupling
• piperidine
• triene

ACKNOWLEDGMENTS

Funding for this project was made possible by a Cottrell College Science Award from the Research Foundation, grant number CC-5918. Thanks to Prof. Bruce Lipshutz at UC Santa Barbara for help in obtaining HRMS of compound 12. Thanks are also given to the CSU, Chico, Department of Chemistry and Biochemistry, and to Prof. David B. Ball for helpful discussions.