Aspidophytine

Aspidophytine
Identifiers
CAS Number	16625-21-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	9958575 ;
PubChem CID	11783895;
CompTox Dashboard (EPA)	DTXSID30472559 ;
	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/s1 Key: QESOHAISGSLAAJ-DHWLSRIRSA-N ;
	SMILES O=C5O[C@@]63N2CCC[C@@]6(\C=C/[C@H]4N(c1c(ccc(OC)c1OC)[C@@]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 [77 °F], 100 kPa).
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	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. 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]

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)
Column: Totally Synthetic, by Paul Docherty, at the Royal Society of Chemistry; published October 9, 2009; retrieved October 3, 2014
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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[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)

[TotallySynthetic-5] Column: Totally Synthetic, by Paul Docherty, at the Royal Society of Chemistry; published October 9, 2009; retrieved October 3, 2014

[LethalChemistry-6] Lethal Chemistry at Harvard, by Stephen S> Hall, in the New York Times; published November 29, 1998; retrieved October 3, 2014