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Structure and absolute configuration of a visamminol derivative using IR and vibrational circular dichroism |
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| Authors: | Eleuterio Burgueño-Tapia Cynthia Ordaz-Pichardo Abigail I Buendía-Trujillo Francisco J Chargoy-Antonio Pedro Joseph-Nathan |
| Institution: | 1. Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala, Col. Santo Tomás, México D.F. 11340, Mexico;2. Escuela Nacional de Medicina y Homeopatía, Instituto Politécnico Nacional, Guillermo Massieu Helguera 239, Col. La Escalera, México D.F. 07320, Mexico;3. Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado 14-740, México D.F. 07000, Mexico |
| Abstract: | The aerial parts of Arracacia tolucensis (Kunth) Hemsl. (Apiaceae) provided the new visamminol derivative (S)-(+)-4′-O-angeloylvisamminol (1), along with the known angular pyranocoumarin 2. Analysis of HMBC NMR correlations did not allow distinction of the linear dihydrofurochromone 1 from pyranochromone 5. The structure and S absolute configuration of (+)-1 was therefore established by comparison of the IR and vibrational circular dichroism spectra of the natural product with the DFT B3LYP/DGDZVP calculated spectra for (S)-1 and (S)-5. Structural verification followed by single crystal X-ray diffraction of (+)-1 and chemical correlation. |
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