Group Meeting Presentation Reports on the Total Synthesis of Ibogaine University of California Davis Group Meeting Presentation Reports on the Total Synthesis of Ibogaine Jesus Cordova Guerrero Olson Research Group May 27th, 2016 Escuela de Ciencias de la Salud Universidad Autónoma de Baja California

Tabernaemontane species Ibogaine: structure and biological activity Tabernanthe or Tabernaemontane species Apocynaceae family Monoterpene indole alkaloid: indole + isoquinuclidine + 7-membered azepane Biology: Potent psychoactive agent Demethylation – noribogaine Antifungal, antilipase, anti HIV, anti-cholinesterasic activity University of California Davis Escuela de Ciencias de la Salud Universidad Autónoma de Baja California 2

7 or less steps, ?% overall yield Ibogaine: total syntheses 2012, Sinha et al. 8 steps, 9.8% overall yield Jana, G.K.; Sinha, S. Tetrahedron 2012, 68, 7155-7165. 1966, Ziegler et al. Buchi, G.; Coffen, D. L.; Kocsis, K.; Sonnet, P. E.; Ziegler, F. E. J. Am. Chem. Soc.1966, 88, 3099. 2016, She et al. 12 steps, 14.5% overall yield Gaoyuan Zhao, G.; Xie, X.; Sun, H.; Yuan, Z.; Zhong, Z.; Tang, S.; She, X. Organic Letters 2016 18 (10), 2447-2450 . 2016, Olson et al. 7 or less steps, ?% overall yield University of California Davis Escuela de Ciencias de la Salud Universidad Autónoma de Baja California 3

Total synthesis of ibogaine by She et al. (±)-tabertinggine, (±)-ibogamine, (±)-ibogaine, (±)-ibogaine hydroxyindolenine, (±)-3-oxoibogaine hydroxyindolenine, (±)-iboluteine, and (±)-ervaoffines D University of California Davis Escuela de Ciencias de la Salud Universidad Autónoma de Baja California 4

Total synthesis of ibogaine by She et al. Synthesis of tabertinggine and 12-methoxy tabertinggine advanced intermediate University of California Davis Escuela de Ciencias de la Salud Universidad Autónoma de Baja California 5

Total synthesis of ibogaine by She et al. Synthesis of (±)-ibogamine University of California Davis Escuela de Ciencias de la Salud Universidad Autónoma de Baja California 6

Total synthesis of ibogaine by She et al. Synthesis of (±)-ibogaine, (±)-ibogaine hydroxyindolenine, (±)-3-oxoibogaine hydroxyindolenine, (±)-iboluteine, and (±)-ervaoffines D

Total synthesis of ibogaine by Sinha et al. University of California Davis Escuela de Ciencias de la Salud Universidad Autónoma de Baja California 8

Thank you 8 Escuela de Ciencias de la Salud Universidad Autónoma de Baja California 8