Aspidophytine Explained

Aspidophytine is an indole alkaloid that has attracted a lot of attention from synthetic chemists.^{[1] [2] [3] [4]} An extract of the cockroach plant, aspidophytine is an insecticidal substance particularly effective against cockroaches. It is one of the two components of the dimer haplophytine.^[5]

In his suicide note, Harvard doctoral student Jason Altom mentioned his stress in attempting to devise a synthetic pathway for the aspidophytine sub-unit of haplophytine as a contributing factor to his psychological breakdown.^[6]

Notes and References

1. "Enantioselective Total Synthesis of Aspidophytine"  He, F.; Bo, Y.; Altom, J. D.; Corey, E. J. J. Am. Chem. Soc. 1999, 121(28), 6771–6772
2. "Stereocontrolled total synthesis of (−)-aspidophytine"  Sumi, S.; Matsumoto, K.; Tokuyama, H.; Fukuyama, T. Tetrahedron 2003, 59, 8571–8587
3. "Application of the Rh(II) Cyclization/Cycloaddition Cascade for the Total Synthesis of (±)-Aspidophytine"   Mejia-Oneto, J. M., Padwa, A. Org. Lett. 2006, 8, 3275–3278
4. "A Concise Asymmetric Total Synthesis of Aspidophytine"  Nicolaou, K. C., Dalby, S. M., Majumder, U. J. Am. Chem. Soc. 2008, 130(45), 14942–14943
5. http://www.rsc.org/chemistryworld/Issues/2009/October/ColumnTotallySynthetic.asp Column: Totally Synthetic
6. https://www.nytimes.com/1998/11/29/magazine/lethal-chemistry-at-harvard.html Lethal Chemistry at Harvard