The first enantioselective total syntheses of intriguing indole alkaloids (+)-condylocarpine (above), (+)-isocondylocarpine and (+)-tubotaiwine was possible with high enantiomeric purity (greater than 99:1).

The syntheses were possible using (1S,5R)-hexahydro-1,5-methano-1H-azocino[4,3-b]indole-12-one as starting material and proceeded via five or six isolated intermediates. The work offers up new insights into how to modify this compound to make other useful products as well as providing a route to these natural products for medicinal screening for anti-inflammatory and analgesic effect.

• Total Synthesis of (+)-Condylocarpine, (+)-Isocondylocarpine, and (+)-Tubotaiwine
  C. L. Martin, S. Nakamura, R. Otte, L. E. Overman,
  Org. Lett. 2010.
  DOI: 10.1021/ol102709s