Aspidospermidine

Aspidospermidine is an alkaloid isolated from plants in the genus Aspidosperma.[1] It has been a popular target for total synthesis,[2][3][4][5] due in part to the fact that it provides a good showcase for synthetic strategies but also because the structure is similar to many other important bioactive molecules.[6]

Aspidospermidine
Names
IUPAC name
(3aR,10bR)-3aβ-Ethyl-2,3,3a,4,5,5aα,6,11,12,13aβ-decahydro-1H-indolizino[8,1-cd]carbazole
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C19H26N2/c1-2-18-9-5-12-21-13-11-19(17(18)21)14-6-3-4-7-15(14)20-16(19)8-10-18/h3-4,6-7,16-17,20H,2,5,8-13H2,1H3/t16-,17-,18-,19-/m1/s1
    Key: YAAIPCQYJYPITK-NCXUSEDFSA-N
  • InChI=1/C19H26N2/c1-2-18-9-5-12-21-13-11-19(17(18)21)14-6-3-4-7-15(14)20-16(19)8-10-18/h3-4,6-7,16-17,20H,2,5,8-13H2,1H3/t16-,17-,18-,19-/m1/s1
    Key: YAAIPCQYJYPITK-NCXUSEDFBY
  • CC[C@]12CCCN3[C@H]1[C@]4(CC3)c5ccccc5N[C@@H]4CC2
Properties
C19H26N2
Molar mass 282.431 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Deutsch, Harold F.; Evenson, Merle A.; Drescher, Peter; Sparwasser, Christoph; Madsen, Paul O. (October 1994). "Isolation and biological activity of aspidospermine and quebrachamine from an Aspidosperma tree source". Journal of Pharmaceutical and Biomedical Analysis. 12 (10): 1283–1287. doi:10.1016/0731-7085(94)00066-2. PMID 7841224.
  2. Marino, Joseph P.; Rubio, Maria B.; Cao, Ganfeng; de Dios, Alfonso (November 2002). "Total Synthesis of (+)-Aspidospermidine: A New Strategy for the Enantiospecific Synthesis of Aspidosperma Alkaloids". Journal of the American Chemical Society. 124 (45): 13398–13399. doi:10.1021/ja026357f. PMID 12418888.
  3. Jones, Spencer B.; Simmons, Bryon; Mastracchio, Anthony; MacMillan, David W. C. (13 July 2011). "Collective synthesis of natural products by means of organocascade catalysis". Nature. 475 (7355): 183–188. doi:10.1038/nature10232. PMC 3439143. PMID 21753848.
  4. Ma, Haichen; Xie, Xingang; Jing, Peng; Zhang, Weiwei; She, Xuegong (2015). "Concise total synthesis of (±)-aspidospermidine". Org. Biomol. Chem. 13 (18): 5255–5259. doi:10.1039/C5OB00228A. PMID 25856579.
  5. Callaghan, Owen; Lampard, Christopher; Kennedy, Alan R.; Murphy, John A. (1999). "A novel total synthesis of (±)-aspidospermidine". Journal of the Chemical Society, Perkin Transactions 1 (8): 995–1002. doi:10.1039/A900335E.
  6. Anagnostaki, Elissavet E.; Zografos, Alexandros L. (2012). ""Common synthetic scaffolds" in the synthesis of structurally diverse natural products". Chemical Society Reviews. 41 (17): 5613–25. doi:10.1039/c2cs35080g. PMID 22782134.
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