Angew. Chem. Int. Ed. doi:10.1002/anie.200902192 (2009)

Powdered leaves from the Mexican cockroach plant, Haplophyton cimicidum, have been used to poison cockroaches and to repel fleas for hundreds of years. And attempts to synthesize one of the plant's active ingredients — the indole alkaloid (+)-haplophytine — have frustrated organic chemists ever since its complex molecular structure was solved in 1973.

Hidetoshi Tokuyama at Tohoku University in Sendai, Japan, and his colleagues now report the first total synthesis of (+)-haplophytine, creating 4.2 milligrams of the molecule. In a key step, the researchers performed an internal rearrangement to create the left-hand segment of the molecule. They then used a traditional Fischer indole synthesis to join that, through a central bond, to the previously synthesized right-hand segment.