Cycloclavine was initially isolated from the seeds of African morning glory Ipomoea hildebrandtii,1a and later from Aspergillus japonicus.1b A recent study showed that cycloclavine exhibits promising insecticidal, antiparasitic, and anticancer properties.2 Cycloclavine possesses a pentacyclic indole framework along with three contiguous stereogenic centers, out of which two adjacent quaternary carbons are part of a cyclopropane ring.3 In this presentation, known strategies for the synthesis of cycloclavine will be discussed (Scheme 1).

Scheme 1: Reported strategies for the synthesis of cycloclavine.
Recently our group developed a one-pot SET oxidative cyclization method for the synthesis of structurally complex cyclopropane-fused cyclic amidines using Cu(II) catalyst.4 Our objective is to explore the total synthesis of cycloclavine using SET oxidative cyclization as a key strategy.
References:
1. (a) Stauffacher, P., Niklaus, H., Tscherter, H. P., Weber, Hofmann, A., Tetrahedron, 1969, 25, 5879-5887; (b) Furuta, T., Koike, M., Abe, M., Agric. Biol. Chem., 1982, 46, 1921-1922.
2. Deng, L., Chen, M., Dong, G., J. Am. Chem. Soc., 2018, 140, 9652-9658.
3. Petronijevic, F. R., Wipf, P., J. Am. Chem. Soc., 2011, 133, 7704-7707.
4. Kirana, D. V., Kanak, K. D., Baskaran, S., Angew. Chem. Int. Ed., 2017, 56, 16197-16201.