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Strictamine

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Strictamine
Names
IUPAC name methyl (10S,12R,13E,18S)-13-Ethylidene-8,15-diazapentacyclooctadeca-2,4,6,8-tetraene-18-carboxylate
Other names Desacetyldesformoakuammiline; Vincamidine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
InChI
  • InChI=1S/C20H22N2O2/c1-3-12-11-22-9-8-20-14-6-4-5-7-15(14)21-18(20)16(22)10-13(12)17(20)19(23)24-2/h3-7,13,16-17H,8-11H2,1-2H3/b12-3-/t13-,16-,17+,20?/m0/s1Key: LITYYRLWHAQJQS-PHDDPKRUSA-N
SMILES
  • C/C=C\1/CN2CCC34(1C2C3=NC5=CC=CC=C45)C(=O)OC
Properties
Chemical formula C20H22N2O2
Molar mass 322.408 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Strictamine is an alkaloid isolated from Alstonia scholaris.

Because of its unusual chemical structure, it has attracted research interest and several laboratory syntheses have been reported.

References

  1. Bhattacharya, S. K.; Bose, R.; Dutta, S. C.; Ray, A. B.; Guha, S. R. (1979). "Neuropharmacological studies on strictamine isolated from Alstonia scholaris". Indian Journal of Experimental Biology. 17 (6): 598–600. PMID 500142.
  2. Smith, Myles W.; Zhou, Zhiyao; Gao, Alison X.; Shimbayashi, Takuya; Snyder, Scott A. (2017). "A 7-Step Formal Asymmetric Total Synthesis of Strictamine via an Asymmetric Propargylation and Metal-Mediated Cyclization". Organic Letters. 19 (5): 1004–1007. doi:10.1021/acs.orglett.6b03839. PMID 28253628.
  3. Li, Wenfei; Chen, Zhitao; Yu, Di; Peng, Xin; Wen, Guohua; Wang, Siqi; Xue, Fei; Liu, Xiao-Yu; Qin, Yong (2019). "Asymmetric Total Syntheses of the Akuammiline Alkaloids (−)-Strictamine and (−)-Rhazinoline". Angewandte Chemie International Edition. 58 (18): 6059–6063. doi:10.1002/anie.201901074. PMID 30775833. S2CID 73472189.
  4. Moreno, Jesus; Picazo, Elias; Morrill, Lucas A.; Smith, Joel M.; Garg, Neil K. (2016). "Enantioselective Total Syntheses of Akuammiline Alkaloids (+)-Strictamine, (−)-2(S)-Cathafoline, and (−)-Aspidophylline A". Journal of the American Chemical Society. 138 (4): 1162–1165. doi:10.1021/jacs.5b12880. PMC 5154302. PMID 26783944.
  5. Xiao, Tao; Chen, Zhi-Tao; Deng, Lin-Feng; Zhang, Dan; Liu, Xiao-Yu; Song, Hao; Qin, Yong (2017). "Formal total synthesis of the akuammiline alkaloid (+)-strictamine". Chemical Communications. 53 (94): 12665–12667. doi:10.1039/C7CC08153G. PMID 29167841.
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