Studies toward the total synthesis of Koumine

ORGN 281

James D White, james.white@orst.edu and David C. Ihle, ihled@onid.orst.edu. Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, OR 97331-4003
Koumine, isolated from the Chinese medicinal plant Kou-wen, is a member of the tetrahydro-β-carboline sub-group of the indole alkaloids and possesses a complex three-dimensional cage structure. Our efforts toward the total synthesis of koumine utilize a tandem [2+2] cycloaddition/retro-Mannich reaction to provide spiro-fused 6,5-bicyclic imine 2. The construction of tricycle 3 and studies toward the completion of koumine will be presented.