Tesis doctorales: TESEO

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Ministerio de Universidades - Gobierno de España

Título: PHOTOCHEMICAL STUDIES TOWARD THE SYNTHESIS OF NATURAL PRODUCTS
Autor: Lejeune, Guillaume
Universidad: Universidad Autónoma de Barcelona
Departamento: QUIMICA ORGANICA
Fecha de Lectura: 12/02/2015
Programa de doctorado: RD 56/2005
Dirección:
- ALIBES ARQUES, RAMÓN (DIRECTOR)
- FIGUEREDO GALIMANY, MARTA (DIRECTOR)
Tribunal:
- Lavilla Grifols, Rodolfo (PRESIDENTE)
- SEBASTIÁN PÉREZ, ROSA MARÍA (SECRETARIO)
- Roscini, Claudio (VOCAL)
Descriptores:
- FOTOQUIMICA
- QUIMICA ORGANICA
- SINTESIS QUIMICA
Localización: BIBLIOTECA DE COMUNICACIÓN Y HEMEROTECA GENERAL UAB
Marcador: https://www.educacion.gob.es/teseo/mostrarRef.do?ref=1137009Añadir a favoritos.
Resumen:
Cyclobutane derivatives are remarkable compounds not only as attractive natural products, as in the pheromone field where several structures bearing a cyclobutane ring are known, but also some cyclobutanes play a crucial role in the pharmaceutical field, as it is the case of several nucleoside analogues that present a strong activity against the replication of some viruses (eg Herpes or HIV). Synthetic organic photochemistry has provided an extremely powerful method for the conversion of simple substrates into more complex products. Several difficulties associated with the performance of preparative photoreactions on large scale have been perceived to be a serious problem to be solved before their routine application. The present thesis has been focused on the study of the potential of different substituted 2(5H)-furanones as precursors of pyran through the formation of bicyclic compounds which could give access to a family of specific trisubsituted tetrahydropyrans. We have developed a photochemical route to access stereocontrolled 2,3,5-trisubstituted THP¿s from furanone in a two step synthesis. Also we have investigated the potential of different substituted maleimides as precursor of conformationally restricted amino acid derivatives and azepane throught the formation of tricyclic compounds by photochemistry. We have synthesized different precursors of amino acid analogues from substituted maleimide, we did not accomplished the synthesis of azepane derivatives, but the amino acid derivatives, synthesized from tricyclic cyclobutene and cyclobutane derivatives, can have a biological activity against panel of human tumour cell lines. Finally, Oleander scales¿ females, is a cosmopolitan pest, mainly found in tropical and subtropical areas, that causes a general weakening of the tree, dicoloration of leaves, and severe deterioration of the fruit. The use of its sexual pheromone to interfere the communication between the male and female will control the population in the infected area. To achieve this control, it is of first importance to be able to synthesize the sexual pheromone active compound. This pheromone presents structural characteristics common to (+)-grandisol, synthesized in our research group, such as two of the acyclic chains linked to the cyclobutane and the configuration of the stereogenic centres. These similarities suggested us the possibility of adapting the synthetic pathway previously designed for (+)-grandisol to the sexual pheromone of Aspidiotus nerii. The principal modification of the former synthesis of grandisol will be the introduction of the terpenic chain in the cyclobutane ring. We have synthesized two advanced intermediates toward the synthesis of the sexual pheromone.

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