Synthesis Workshop: Total Synthesis of Chilocorine C with Vlad Lisnyak (Episode 24)

In this episode, we are joined by Vlad Lisnyak (Snyder Group, University of Chicago) who takes us through his recent total synthesis of chilocorine C. Parent reference: J. Am. Chem. Soc. 2020, 142, 12027-12033 Other references (in order of appearance): King, A. G.; Meinwald, J. Chem. Rev. 1996, 96, 1105 Huang, Q.; Attygalle, A. B.; Meinwald, J.; Houck, M. A.; Eisner, T. J. Nat. Prod. 1998, 61, 598 Gao, A. X.; Hamada, T.; Snyder, S. A. Angew. Chem. Int. Ed. 2016, 55, 10301 Lawson, E. C. et. al. Bioorg. Med. Chem. 2006, 14, 4208 Abraham, H.; Stella, L. Tetrahedron 1992, 48, 9707 German patent: DE 19616049A1 Osborn, J. A.; Schrock, R. R. J. Am. Chem. Soc. 1971, 93, 2397 Murahashi, S.-I.; Imada, Y.; Ohtake, H. J. Org. Chem. 1994, 59, 6170 Ohtake, H.; Imada, Y.; Murahashi, S.-I. J. Org. Chem. 1999, 64, 3790 Lisnyak V. G.; Lynch-Colameta, T.; Snyder, S. A. Angew. Chem. Int. Ed. 2018, 57, 15162 Curran, D. P. J. Am. Chem. Soc. 1983, 105, 5826 Cicchi, S.; Goti, A.; Brandi, A.; Guarna, A.; De Sarlo, F. Tetrahedron Lett. 1990, 31, 3351 Zimmer, R.; Collas, M.; Roth, M.; Reißig, H.-U. Liebigs Ann. Chem. 1992, 1992, 709 Bode, J. W.; Carreira, E. M. Org. Lett. 2001, 3, 1587 Miyano, S.; Yamashita, O.; Sumoto, K.; Shima, K.; Hayashimatsu, M.; Satoh, F. J. Heterocycl. Chem. 1987, 47 Stevens, R. V. Acc. Chem. Res. 1984, 17, 289 Weidner, J.; Vilsmaier, E.; Fries, Rao, A. X. Monatsh. Chem. 1987, 118, 1039 Li, J.-H.; Chen, Z.-C. Synth. Commun. 2000, 30, 2317 Oka, M.; Baba, K.; Suzuki, T.; Matsumoto, Y. Heterocycles 1997, 45, 2317 Alt, G. H.; Gallegos, G. A. J. Org. Chem. 1971, 36, 1000 Ghaffar, T.; Parkins, A. W. Tetrahedron Lett. 1995, 36, 8657 Lazbin, I. M.; Koser, G. F. J. Org. Chem. 1986, 51, 2669 Srogl, J.; Voltrova, S. Org. Lett. 2009, 11, 843 Gao, A. X.; Hamada, T.; Snyder, S. A. Angew. Chem. Int. Ed. 2016, 55, 10301 Prato, M.; Quintily, U.; Scorrano, G.; Sturaro, A. Synthesis, 1982, 679