Aspidophytine
| Aspidophytine |
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| Identifiers |
| CAS number |
16625-21-1 |
| PubChem |
11783895 |
| ChemSpider |
9958575 Y |
| Jmol-3D images |
Image 1 |
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O=C5O[C@@]63N2CCC[C@@]6(\C=C/[C@H]4N(c1c(ccc(OC)c1OC)[C@@]34CC2)C)C5
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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 Y
Key: QESOHAISGSLAAJ-DHWLSRIRSA-N Y
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| Properties |
| Molecular formula |
C22H26N2O4 |
| Molar mass |
382.45 g/mol |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
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.
The suicide note of Harvard doctoral student Jason Altom refers specifically to his stress in trying to synthesize the molecule.
References
- ^ "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)
- ^ "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)
- ^ "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)
- ^ "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)