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Synthesis Workshop: Electrochemical Terpene Synthesis with Maximilian Palkowitz (Episode 95)

In this Research Spotlight episode, Maximilian Palkowitz (Baran lab, Scripps) joins us to share his work on terpene synthesis via mild electrochemical coupling reactions. Key reference: Science 2022, 375, 745-752. http://doi.org/10.1126/science.abn1395 A Survival Guide for the “Electro-curious”: Acc. Chem. Res. 2020, 53, 1, 72–83. http://doi.org/10.1021/acs.accounts.9... Other references (in order of appearance): 1) Kingston, C.; Palkowitz, M. D.; Takahira, Y.; Vantourout, J. C.; Peters, B. K.; Kawamata, Y.; Baran, P. S. Acc. Chem. Res. 2020, 53, 72-83. 2) Ding, H.; DeRoy, P. L.; Perreault, C.; Larivée, A.; Siddiqui, A.; Caldwell, C. G.; Harran, S.; Harran, P. G. Angew. Chem. Int. Ed. 2015, 54, 4818-4822. 3) Sibille, S.; d'Incan, E.; Leport, L.; Perichon, J. Tetrahedron Lett. 1986, 27, 3129-3132. 4) Putter H.; Hannebaum, H. US6063256 Johnson, W. S.; Gravestock, M. B.; McCarry, B. E. J. Am. Chem. Soc. 1971, 93, 4332-4334. Other polyene platform syntheses: Negishi, E.-i.; Wang, G.; Rao, H.; Xu, Z. J. Org. Chem. 2010, 75, 3151-3182. Lee, S. J.; Gray, K. C.; Paek, J. S.; Burke, M. D. J. Am. Chem. Soc. 2008, 130, 466-468. 1) Cannes, C.; Condon, S.; Durandetti, M.; Périchon, J.; Nédélec, J. Y. J. Org. Chem. 2000, 65, 4575-4583. 2) Perkins, R. J.; Pedro, D. J.; Hansen, E. C. Org. Lett. 2017, 19, 3755-3758. 3) Suzuki, N.; Hofstra, J. L.; Poremba, K. E.; Reisman, S. E. Org. Lett. 2017, 19, 2150-2153. 4) Li, H.; Breen, C. P.; Seo, H.; Jamison, T. F.; Fang, Y.-Q.; Bio, M. M. Org. Lett. 2018, 20, 1338-1341. 5) Koyanagi, T.; Herath, A.; Chong, A.; Ratnikov, M.; Valiere, A.; Chang, J.; Molteni, V.; Loren, J. Org. Lett. 2019, 21, 816-820. 6) Huihui, J. M. M.; Caputo, J. A.; Melchor, Z.; Olivares, A. M.; Spiewak, A. M.; Johnson, K. A.; DiBenedetto, T. A.; Kim, S.; Ackerman, L. K. G.; Weix, D. J. J. Am. Chem. Soc. 2016, 138, 5016-5019. 1) Chillawar, R. R.; Tadi, K. K.; Motghare, R. V. J. Anal. Chem. 2015, 70, 399-418. 2) Noor, A. a. M.; Shahid, M. M.; Rameshkumar, P.; Huang, N. M. Microchimica Acta 2016, 183, 911-916. 3) Karuppiah, C.; Muthupandi, K.; Chen, S.-M.; Ali, M. A.; Palanisamy, S.; Rajan, A.; Prakash, P.; Al-Hemaid, F. M. A.; Lou, B.-S. RSC Advances 2015, 5, 31139-31146. 4) Isse, A. A.; Gottardello, S.; Maccato, C.; Gennaro, A. Electrochem. Commun. 2006, 8, 1707-1712. For more on RDE voltammetry: https://pineresearch.com/shop/kb/theo... 1) Levich, V.G., Physiochemical Hydrodynamics, Prentice Hall, Englewood Cliffs, N.J. (1962). 2) Till, N. A.; Oh, S.; MacMillan, D. W. C.; Bird, M. J. J. Am. Chem. Soc. 2021, 143, 9332–9337. 1) Camelio, A. M.; Johnson, T. C.; Siegel, D. J. Am. Chem. Soc. 2015, 137, 11864-11867. 2) Snider, B. B.; Kiselgod, J. Y.; Foxman, B. M. J. Org. Chem. 1998, 62, 7945-7952.