Synthesis of Polycyclic Natural Products through Skeletal Rearrangement

(1) (a) Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2016, 79, 629. (b) Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2020, 83, 770. (c) Gerry, C. J.; Schreiber, S. L. Nat. Rev. Drug Discov. 2018, 17, 333. (d) Davison, E. K.; Brimble, M. A. Curr. Opin. Chem. Biol. 2019, 52, 1.

(2) (a) Lachance, H.; Wetzel, S.; Kumar, K.; Waldmann, H. J. Med. Chem. 2012, 55, 5989. (b) Kaiser, M.; Wetzel, S.; Kumar, K.; Waldmann, H. Cell. Mol. Life Sci. 2008, 65, 1186.

(3) (a) Lovering, F.; Bikker, J.; Humblet, C. J. Med. Chem. 2009, 52, 6752. (b) Lovering, F. MedChemComm 2013, 4, 515.

(4) (a) Yokoshima, S. Chem. Pharm. Bull. 2013, 61, 251. (b) Yokoshima, S. Yuki Gosei Kagaku Kyokaishi 2017, 75, 1035.

(5) For selected reviews on Diels–Alder reaction, see: (a) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem. Int. Ed. 2002, 41, 1668. (b) Takao, K.; Munakata, R.; Tadano, K. Chem. Rev. 2005, 105, 4779. (c) Foster, R. A. A.; Willis, M. C. Chem. Soc. Rev. 2013, 42, 63. (d) Jiang, X.; Wang, R. Chem. Rev. 2013, 113, 5515. (e) Xie, M.; Lin, L.; Feng, X. Chem. Rec. 2017, 17, 1184. (f) Yang, B.; Gao, S. Chem. Soc. Rev. 2018, 47, 7926.

(6) You, L.; Liang, X.-T.; Xu, L.-M.; Wang, Y.-F.; Zhang, J.-J.; Su, Q.; Li, Y.- H.; Zhang, B.; Yang, S.-L.; Chen, J.-H.; Yang, Z. J. Am. Chem. Soc. 2015, 137, 10120.

(7) Kobayashi, J.; Hirasawa, Y.; Yoshida, N.; Morita, H. J. Org. Chem. 2001, 66, 5901.

(8) (a) Nishimura, T.; Unni, A. K.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2011, 133, 418. (b) Nishimura, T.; Unni, A. K.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2013, 135, 3243.

(9) For other synthese of lyconadin A, see: (a) Beshore, D. C.; Smith, A. B., III. J. Am. Chem. Soc. 2007, 129, 4148. (b) Bisai, A.; West, S. P.; Sarpong, R. J. Am. Chem. Soc. 2008, 130, 7222. (c) Lee, A. S.; Liau, B. B.; Shair, M. D. J. Am. Chem. Soc. 2014, 136, 13442. (d) Yang, Y.; Haskins, C. W.; Zhang, W.; Low, P. L.; Dai, M. Angew. Chem. Int. Ed. 2014, 53, 3922. (e) Yang, Y.; Dai, M. Synlett 2014, 25, 2093. (f) Zhang, J.; Yan, Y.; Hu, R.; Li, T.; Bai, W.-J.; Yang, Y. Angew. Chem. Int. Ed. 2020, 59, 2860.

(10) (a) Nilsson, B. L.; Overman, L. E.; Read De Alaniz, J.; Rohde, J. M. J. Am. Chem. Soc. 2008, 130, 11297. (b) Altman, R. A.; Nilsson, B. L.; Overman, L. E.; Read De Alaniz, J.; Rohde, J. M.; Taupin, V. J. Org. Chem. 2010, 75, 7519.

(11) Fujii, M.; Nishimura, T.; Koshiba, T.; Yokoshima, S.; Fukuyama, T. Org. Lett. 2013, 15, 232.

(12) Tan, C.-H.; Ma, X.-Q.; Chen, G.-F.; Zhu, D.-Y. Helv. Chim. Acta 2002, 85, 1058.

(13) Tanimura, S.; Yokoshima, S.; Fukuyama, T. Org. Lett. 2017, 19, 3684.

(14) For other syntheses of huperzine Q, see: (a) Nakayama, A.; Kogure, N.; Kitajima, M.; Takayama, H. Angew. Chem. Int. Ed. 2011, 50, 8025. (b) Hong, B.; Li, H.; Wu, J.; Zhang, J.; Lei, X. Angew. Chem. Int. Ed. 2015, 54, 1011. (c) Zeng, C.; Zhao, J.; Zhao, G. Tetrahedron 2015, 71, 64. (d) Hong, B.; Hu, D.; Wu, J.; Zhang, J.; Li, H.; Pan, Y.; Lei, X. Chem. Asian J. 2017, 12, 1557.

(15) House, H. O.; Wasson, R. L. J. Am. Chem. Soc. 1957, 79, 1488.

(16) For selected reviews on biomimetic synthesis of natural products, see: (a) Bulger, P. G.; Bagal, S. K.; Marquez, R. Nat. Prod. Rep. 2008, 25, 254. (b) Kim, J.; Movassaghi, M. Chem. Soc. Rev. 2009, 38, 3035. (c) Poupon, E. Planta Med. 2012, 78, IL44. (d) Jürjens, G.; Kirschning, A.; Candito, D. A. Nat. Prod. Rep. 2015, 32, 723. (e) Takayama, H. Chem. Pharm. Bull. 2020, 68, 103.

(17) Tan, C.-H.; Chen, G.-F.; Ma, X.-Q.; Jiang, S.-H.; Zhu, D.-Y. J. Nat. Prod. 2002, 65, 1021.

(18) Kumazaki, H.; Nakajima, R.; Bessho, Y.; Yokoshima, S.; Fukuyama, T. Synlett 2015, 26, 2131.

(19) Nomura, T.; Yokoshima, S.; Fukuyama, T. Org. Lett. 2018, 20, 119.

(20) Donald, J. R.; Unsworth, W. P. Chem. Eur. J. 2017, 23, 8780.

(21) (a) Takayama, H.; Katakawa, K.; Kitajima, M.; Yamaguchi, K.; Aimi, N. Tetrahedron Lett. 2002, 43, 8307. (b) Nakayama, A.; Kogure, N.; Kitajima, M.; Takayama, H. Org. Lett. 2009, 11, 5554.

(22) Churykau, D. H.; Zinovich, V. G.; Kulinkovich, O. G. Synlett 2004, 2004, 1949.

(23) González, A. G.; De La Fuente, G.; Reina, M.; Zabel, V.; Watson, W. H. Tetrahedron Lett. 1980, 21, 1155.

(24) (a) Wiesner, K.; Tsai, T. Y. R.; Huber, K.; Bolton, S. E.; Vlahov, R. J. Am. Chem. Soc. 1974, 96, 4990. (b) Wiesner, K. Tetrahedron 1985, 41, 485. (c) Marth, C. J.; Gallego, G. M.; Lee, J. C.; Lebold, T. P.; Kulyk, S.; Kou, K. G. M.; Qin, J.; Lilien, R.; Sarpong, R. Nature 2015, 528, 493. (d) Kou, K. G. M.; Kulyk, S.; Marth, C. J.; Lee, J. C.; Doering, N. A.; Li, B. X.; Gallego, G. M.; Lebold, T. P.; Sarpong, R. J. Am. Chem. Soc. 2017, 139, 13882. (e) Kamakura, D.; Todoroki, H.; Urabe, D.; Hagiwara, K.; Inoue, M. Angew. Chem. Int. Ed. 2020, 59, 479.

(25) Gin and coworkers accomplished a synthesis of an aconitine-type norditerpenoid alkaloid, neofinaconitine, without using the Wagner–Meerwein rearrangement: Shi, Y.; Wilmot, J. T.; Nordstrøm, L. U.; Tan, D. S.; Gin, D. Y. J. Am. Chem. Soc. 2013, 135, 14313.

(26) (a) Nishiyama, Y.; Yokoshima, S.; Fukuyama, T. Org. Lett. 2016, 18, 2359. (b) Nishiyama, Y.; Yokoshima, S.; Fukuyama, T. Org. Lett. 2017, 19, 5833.

(27) Nishiyama, Y.; Han-Ya, Y.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2014, 136, 6598.

(28) For reviews on the oxidative dearomatization/Diels–Alder reaction sequence, see: (a) Liao, C.-C.; Peddinti, R. K. Acc. Chem. Res. 2002, 35, 856. (b) Magdziak, D.; Meek, S. J.; Pettus, T. R. R. Chem. Rev. 2004, 104, 1383. (c) Pouységu, L.; Deffieux, D.; Quideau, S. Tetrahedron 2010, 66, 2235. (d) Roche, S. P.; Porco Jr, J. A. Angew. Chem. Int. Ed. 2011, 50, 4068. (e) Liu, X.-Y.; Qin, Y. Nat. Prod. Rep. 2017, 34, 1044.

(29) For selected reviews on ring-closing metathesis, see: (a) Kotha, S.; Meshram, M.; Khedkar, P.; Banerjee, S.; Deodhar, D. Beilstein J. Org. Chem. 2015, 11, 1833. (b) Han, J.-C.; Li, C.-C. Chem. Rec. 2017, 17, 499. (c) Lecourt, C.; Dhambri, S.; Allievi, L.; Sanogo, Y.; Zeghbib, N.; Ben Othman, R.; Lannou, M. I.; Sorin, G.; Ardisson, J. Nat. Prod. Rep. 2018, 35, 105. (d) Kotha, S.; Meshram, M.; Dommaraju, Y. Chem. Rec. 2018, 18, 1613. (e) Cheng-Sánchez, I.; Sarabia, F. Synthesis 2018, 50, 3749.

(30) (a) Miura, Y.; Hayashi, N.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2012, 134, 11995. (b) Hayashi, N.; Miura, Y.; Yokoshima, S.; Fukuyama, T. Chem. Pharm. Bull. 2019, 67, 64.

(31) For other synthese of isoschizogamine, see: (a) Hubbs, J. L.; Heathcock, C. H. Org. Lett. 1999, 1, 1315. (b) Wang, X.; Xia, D.; Tan, L.; Chen, H.; Huang, H.; Song, H.; Qin, Y. Chem. Eur. J. 2015, 21, 14602. (c) Takada, A.; Fujiwara, H.; Sugimoto, K.; Ueda, H.; Tokuyama, H. Chem. Eur. J. 2015, 21, 16400. (d) Xu, Z.; Bao, X.; Wang, Q.; Zhu, J. Angew. Chem. Int. Ed. 2015, 54, 14937.

(32) (a) Renner, U. Lloydia 1964, 27, 406. (b) Hájíček, J.; Taimr, J.; Buděšínský, M. Tetrahedron Lett. 1998, 39, 505.

(33) Kleinfelter, D. C.; Gerteisen, T. J. J. Org. Chem. 1971, 36, 3255.

(34) Stewart, I. C.; Ung, T.; Pletnev, A. A.; Berlin, J. M.; Grubbs, R. H.; Schrodi, Y. Org. Lett. 2007, 9, 1589.

(35) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000.

(36) Murakami, K.; Toma, T.; Fukuyama, T.; Yokoshima, S. Angew. Chem. Int. Ed. 2020, 59, 6253.

(37) For our other results on skeletal rearranegement, see: (a) Yamada, R.; Fukuyama, T.; Yokoshima, S. Org. Lett. 2018, 20, 4504. (b) Watanabe, S.; Ishikawa, M.; Nomura, T.; Fukuyama, T.; Yokoshima, S. Synlett 2018, 29, 2377.