Strictamine

Strictamine
	source ↗
Names
	IUPAC name methyl (10S,12R,13E,18S)-13-Ethylidene-8,15-diazapentacyclo[10.5.1.01,9.02,7.010,15]octadeca-2,4,6,8-tetraene-18-carboxylate
	Other names Desacetyldesformoakuammiline; Vincamidine
Identifiers
CAS Number	6475-05-4;
3D model (JSmol)	Interactive image;
ChemSpider	21270082;
PubChem CID	6444325;
	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/s1 Key: LITYYRLWHAQJQS-PHDDPKRUSA-N;
	SMILES C/C=C\1/CN2CCC34[C@H]([C@H]1C[C@H]2C3=NC5=CC=CC=C45)C(=O)OC;
Properties
Chemical formula	C20H22N2O2
Molar mass	322.408 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

Strictamine is an alkaloid isolated from Alstonia scholaris.¹

Because of its unusual chemical structure, it has attracted research interest and several laboratory syntheses have been reported.²³⁴⁵

References

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.
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.
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.
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.
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.