4,21-Dehydrogeissoschizine

4,21-Dehydrogeissoschizine
Names
IUPAC name
(16Z)-17-Hydroxy-16-(methoxycarbonyl)-4,16,17,19,20,21-hexadehydro-17,18-seco-4λ5-yohimban-4-ylium
Preferred IUPAC name
(2S,3E,12bS)-3-Ethylidene-2-[(1Z)-1-hydroxy-3-methoxy-3-oxoprop-1-en-2-yl]-2,3,6,7,12,12b-hexahydro-1H-5λ5-indolo[2,3-a]quinolizin-5-ylium
Identifiers
CAS Number
  • 73385-56-5
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17294
ChemSpider
  • 4444227
PubChem CID
  • 5280619
UNII
  • Z3D2Q8C832 checkY
CompTox Dashboard (EPA)
  • DTXSID90415063 Edit this at Wikidata
InChI
  • InChI=1S/C21H22N2O3/c1-3-13-11-23-9-8-15-14-6-4-5-7-18(14)22-20(15)19(23)10-16(13)17(12-24)21(25)26-2/h3-7,11-12,16,19,22H,8-10H2,1-2H3/p+1/b13-3-/t16-,19-/m0/s1
    Key: CUHFIPBCFIPFJM-JXSBNBLESA-O
  • InChI=1/C21H22N2O3/c1-3-13-11-23-9-8-15-14-6-4-5-7-18(14)22-20(15)19(23)10-16(13)17(12-24)21(25)26-2/h3-7,11-12,16,19,22H,8-10H2,1-2H3/p+1/b13-3-/t16-,19-/m0/s1
    Key: CUHFIPBCFIPFJM-XNRICKBFBB
  • [H][C@@]12C[C@H](\C(=C\O)C(=O)OC)\C(=C/C)C=[N+]1CCC1=C2NC2=CC=CC=C12
Properties
Chemical formula
 C21H23N2O3
Molar mass 351.426 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
Chemical compound

4,21-Dehydrogeissoschizine is a terpene indole alkaloid.[1] It is believed to be the precursor leading to the formation of the aspidosperma, corynanthe, and iboga classes of terpene indole alkaloids.

References

  1. ^ Rueffer, Martina; Kan-Fan, Christiane; Husson, Henri-Phillipe; Stöckigt, Joachim; Zenk, Meinhart H (1979). "4,21-Dehydrogeissoschizine, an intermediate in heteroyohimbine alkaloid biosynthesis". J. Chem. Soc., Chem. Commun. (22): 1016–1018. doi:10.1039/C39790001016.


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