700813-16-7Relevant academic research and scientific papers
Hypervalent Iodine(III)-Mediated Cascade Cyclization of Propargylguanidines and Total Syntheses of Kealiinine B and C
Tian, Guilong,Fedoseev, Pavel,Van der Eycken, Erik V.
supporting information, p. 5224 - 5227 (2017/04/24)
An oxidative cascade cyclization of propargylguanidines promoted by phenyliodonium diacetate (PIDA) was developed. The protocol provides an efficient route for the synthesis of the alkaloids kealiinines B and C as well as homologues. The difference in the electronic nature of the acetylene substituent resulted in two ways of the cyclization. A plausible mechanism is proposed based on the experimental results.
Synthesis of the reported structures for kealiinines B and C
Gibbons, Joseph B.,Gligorich, Keith M.,Welm, Bryan E.,Looper, Ryan E.
, p. 4734 - 4737 (2013/01/15)
Syntheses of the reported structures of kealiinines B and C have been executed. An intermolecular electrophile-induced cyclization of a pendant arene on an ene-guanidine affords the tetracyclic, oxidized naphthimidazole cores.
Total syntheses of kealiinines A-C
Das, Jayanta,Koswatta, Panduka B.,Jones, J. Daniel,Yousufuddin, Muhammed,Lovely, Carl J.
supporting information, p. 6210 - 6213 (2013/02/23)
Short total syntheses of the Leucetta-derived alkaloids, kealiinines A-C, have been accomplished using an intramolecular Friedel-Crafts-dehydration sequence of a bis benzylic diol. The precursor diol was obtained through a series of position-specific Grignard reactions from 1-methyl-4,5- diiodoimidazole. C2-Azidation and hydrogenation of the azide then provided the reported structures of kealiinines A-C. While the 1H NMR data did not completely match for these materials, the HPLC data were consistent with the assigned structure of these alkaloids.
