Transition metal complexes in organic synthesis, part 55. Synthesis of corannulene via an iron-mediated [2+2+1] cycloaddition
✍ Scribed by Hans-Joachim Knölker; Arnold Braier; Dirk J. Bröcher; Peter G. Jones; Holger Piotrowski
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 218 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
þ)-Demethoxycarbonyldihydrogambirtannine was obtained in six steps and 49% overall yield from 3,4-dihydro-b-carboline using an iron-mediated [2+2+1] cycloaddition as the key-step. Oxidation of (þ)-demethoxycarbonyldihydrogambirtannine led to norketoyobyrine.
A straightforward two-step synthesis of indolo[2,3-b]carbazole using a double iron-mediated arylamine eyelization as the key-step is described.
Evidence for the structure of 13 was provided by the sharp s at 12.67 ppm (phenol OH) in the 'H-NMR spectrum. The substitution pattern was confirmed by NOE difference spectra. Irradiation at the Me signal at 2.28 ppm resulted in a NOE of the aromatic proton at 6.67 ppm.