Synthesis of diversely functionalized pyrrolizidines and indolizidines using olefin ring-closing metathesis

Various nitrogen-fused tricyclic compounds, having benzoindolizidine and benzopyrrolizidines ring systems were synthesized via ene–ene metathesis using the first and second-generation Grubbs catalyst. The ene–ene metathesis proceeded smoothly in refluxing CH 2Cl 2 with 3.0 mol % of G 1 , giving good...

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Bibliographic Details
Published in:Tetrahedron 2009-06, Vol.65 (25), p.4846-4854
Main Authors: Ben-Othman, Raja, Othman, Mohamed, Ciamala, Kabula, Knorr, Michael, Strohmann, Carsten, Decroix, Bernard
Format: Article
Language:English
Subjects:
Benzoindolizidine
Benzopyrrolizidines
Chemical Sciences
Chemistry
Crystal structure
Ene–ene metathesis
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Isoindole
Organic chemistry
Preparations and properties
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Summary:Various nitrogen-fused tricyclic compounds, having benzoindolizidine and benzopyrrolizidines ring systems were synthesized via ene–ene metathesis using the first and second-generation Grubbs catalyst. The ene–ene metathesis proceeded smoothly in refluxing CH 2Cl 2 with 3.0 mol % of G 1 , giving good yields (78–86%) of the benzoindolizidine products 12a, b. The benzopyrrolizidine 6 was prepared after optimization in 64% yield by using 5.0+5.0 mol % of G 2 . The resulting olefin moiety of the indolizidine framework is a suitable precursor for polyhydroxy structures via the Sharpless process. The structures of the polyhydroxylated adducts were determined by 1H NMR spectra and single-crystal X-ray analysis. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.04.039