Total Synthesis - Natural Products

We are interested in the synthesis of alkaloid natural compounds, widely present in nature and offering an endless source of inspiration and creativity. Currently, we are focusing our attention on the lycorine family, salinosporamide derivatives, ß-substituted α-amino acids, ketene chemistry, and reactivity of thiofunctionalized compounds.  Some of these natural products are isolated in unusable yields (small quantities) and often have an incorrect chemical reported structure. In our synthetic studies, we always wish to develop new chemical transformations (or methodologies) and offer efficient and original ways for their synthesis and characterization, but also to allow the access to analogs.

Selected publications

Rulliere, P., Cannillo, A., Grisel, J., Cividino, P., Sebastien, C., & Poisson, J. F. (2018). Total Synthesis of Proteasome Inhibitor (-)-Omuralide through Asymmetric Ketene [2 + 2]-Cycloaddition. Organic Letters, 20 (15), 4558-4561. doi:10.1021/acs.orglett.8b01851

 

Kazak, M., Priede, M., Shubin, K., Bartrum, H. E., Poisson, J. F., & Suna, E. (2017). Stereodivergent Synthesis of Pseudotabersonine Alkaloids. Organic Letters, 19 (19), 5356-5359. doi:10.1021/acs.orglett.7b02635

 

Depres, J. P., Delair, P., Poisson, J. F., Kanazawa, A., & Greene, A. E. (2016). Diverse Natural Products from Dichlorocyclobutanones: An Evolutionary Tale. Accounts of Chemical Research, 49 (2), 252-261. doi:10.1021/acs.accounts.5b00493

 

Bartrum, H. E., Viceriat, A., Carret, S., & Poisson, J. F. (2014). Sulfinylimidates as chiral amide equivalents for irreversible, asymmetric aldol reactions. Organic Letters, 16 (7), 1972-1975. doi:10.1021/ol500520h

 

Orellana, A., Pandey, S. K., Carret, S., Greene, A. E., & Poisson, J. F. (2012). A Diels-Alder-Based Total Synthesis of (-)-Kainic Acid. Journal of Organic Chemistry, 77 (12), 5286-5296. doi:10.1021/Jo300608g
Pandey, S. K., Orellana, A., Greene, A. E., & Poisson, J. F. (2006). High-pressure Diels-Alder approach to natural kainic acid. Organic Letters, 8 (24), 5665-5668.doi:10.1021/ol062419l

 

Darses, B., Greene, A. E., & Poisson, J. F. (2012). Asymmetric Synthesis of Cyclobutanones: Synthesis of Cyclobut-G. Journal of Organic Chemistry, 77 (4), 1710-1721. doi: 10.1021/jo202261z
Darses, B., Greene, A. E., Coote, S. C., & Poisson, J. F. (2008). Expedient approach to chiral cyclobutanones: Asymmetric synthesis of cyclobut-G. Organic Letters, 10 (5), 821-824. doi:10.1021/ol70977x

 

Ceccon, J., Danoun, G., Greene, A. E., & Poisson, J. F. (2009). Asymmetric synthesis of (+)-castanospermine through enol ether metathesis-hydroboration/oxidation. Organic & Biomolecular Chemistry, 7 (10), 2029-2031. doi: 10.1039/b901488h

 

Danoun, G., Ceccon, J., Greene, A. E., & Poisson, J. F. (2009). Stereocontrolled Total Synthesis of (+)-1-Deoxynojirimycin. European Journal of Organic Chemistry, (25), 4221-4224. doi: 10.1002/ejoc.200900595

 

Ceccon, J., Greene, A. E., & Poisson, J. F. (2006). Asymmetric [2+2] cycloaddition: Total synthesis of (-)-swainsonine and (+)-6-epicastanospermine. Organic Letters, 8 (21), 4739-4742. doi: 10.1021/ol0617751

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