Intramolecular Diels-alder Reactions For Synthesis Of Hexahydro-1H-isochromen-1-ones And Hexahydro-1H-isoindol-1-one Core Of Cytochalasin Z8

As a very important organic reaction, intramolecular Diels-Alder reaction is used to produce complicated bicyclic compounds. This thesis expounds the synthesis of hexahydro-1H-isochromen-l-ones via microwave-assisted intramolecular Diels-Alder (IMDA) reactions, and the synthesis of hexahydro-lH-isoindol-1-one fragment of the natural product cytochalasin Z8.Chapter1briefly introduces intramolecular Diels-Alder reactions and the total synthesis of macrolide cytochalasins natural products. Firstly, we introduce the stereochemistry of hexahydro-lH-isochromen-l-ones through intramolecular Diels-Alder reactions. Secondly, we enumerate some applications of intramolecular Diels-Alder reactions in the total synthesis of natural products. Finally, we introduce some synthetic approaches of cytochalasin analogues.Chapter2concerns the synthesis of hexahydro-1H-isochromen-1-ones via microwave-assisted IMDA reactions. We report here on the microwave-assisted IMDA cycloaddition of ester-tethered6-methyl-1,3,9-decatriene for synthesis of the bicyclic δ-pentyrolactones and on the influence of the C6-Me in triene on the diastereoselectivity. The stereochemistry of the isomers is confirmed by comparison to1H NMR of other known compounds which are determined by the X-ray.Chapter3reports the synthesis of hexahydro-1H-isoindol-1-one fragment of cytochalasin Z8. It contains three synthetic routes. We have achieved to convert the C9-H to a reversed C9-OH through leading Boc into amide group.Finally, the experimental section, full characterization data for all products, cited references, some copies of selected original1H NMR and13C NMR spectra and the data of X-ray single crystal are found at the end of the thesis.