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Aspidophytine

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Aspidophytine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: QESOHAISGSLAAJ-DHWLSRIRSA-N
SMILES
  • O=C5O63N2CCC6(\C=C/4N(c1c(ccc(OC)c1OC)34CC2)C)C5
Properties
Chemical formula C22H26N2O4
Molar mass 382.45 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Aspidophytine is an indole alkaloid that has attracted significant attention from synthetic chemists. 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.

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.

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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