Aspidophytine

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]

Aspidophytine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C22H26N2O4/c1-23-16-7-9-20-8-4-11-24-12-10-21(16,22(20,24)28-17(25)13-20)14-5-6-15(26-2)19(27-3)18(14)23/h5-7,9,16H,4,8,10-13H2,1-3H3/t16-,20-,21-,22+/m1/s1 checkY
    Key: QESOHAISGSLAAJ-DHWLSRIRSA-N checkY
  • O=C5O[C@@]63N2CCC[C@@]6(\C=C/[C@H]4N(c1c(ccc(OC)c1OC)[C@@]34CC2)C)C5
Properties
C22H26N2O4
Molar mass 382.45 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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]

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 (doi:10.1021/ja9915201)
  2. "Stereocontrolled total synthesis of (−)-aspidophytine"  Sumi, S.; Matsumoto, K.; Tokuyama, H.; Fukuyama, T. Tetrahedron 2003, 59, 8571–8587 (doi:10.1016/j.tet.2003.09.005)
  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 (doi:10.1021/ol061137i)
  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 (doi:10.1021/ja806176w)
  5. Column: Totally Synthetic, by Paul Docherty, at the Royal Society of Chemistry; published October 9, 2009; retrieved October 3, 2014
  6. Lethal Chemistry at Harvard, by Stephen S> Hall, in the New York Times; published November 29, 1998; retrieved October 3, 2014
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