Aspidospermidine

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
Properties
C19H26N2
Molar mass 282.43 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

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]

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. PMID 7841224. doi:10.1016/0731-7085(94)00066-2.
  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. PMID 12418888. doi:10.1021/ja026357f.
  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. PMC 3439143 Freely accessible. PMID 21753848. doi:10.1038/nature10232.
  4. ↑ Ma, Haichen; Xie, Xingang; Jing, Peng; Zhang, Weiwei; She, Xuegong (2015). "Concise total synthesis of (±)-aspidospermidine". Org. Biomol. Chem. 13 (18): 5255–5259. PMID 25856579. doi:10.1039/C5OB00228A.
  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. PMID 22782134. doi:10.1039/c2cs35080g.


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