Gold(I)-Catalyzed Cycloadditions and their Application in the Synthesis of Natural Product

The potential of gold(I) catalysis on the synthesis of natural products has been widely explored in the last decades. This Doctoral Thesis presents our efforts to expand the applications of gold(I)-catalyzed cycloadditions in total synthesis. First, we have developed a new methodology for acetylene activation by means of gold(I) catalysis, in which the ligand on the gold(I) catalyst can tune the reaction outcome, either for the formation of (Z,Z)-1,3-dienes or towards bis-cyclopropanes. This method was applied to the one-step total synthesis of waitziacuminone. In second place, we have stablished a novel cycloisomerization/cycloaddition cascade which allows for the rapid and efficient construction of hydroazulenes, from enynes and dienes. The mechanism of this reaction was studied experimentally and computationally, finding a strong dependence on the nature of the diene partner and on the gold(I) catalyst employed. Finally, this strategy was applied to a common synthetic route towards aspterric acid, penigrisacid A and schisanwilsonene A. The carbon-skeletons of the three natural products were synthetized and characterized by x-ray diffraction.

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According to the last information received from ICIQ’s safety department about the measures to prevent and contain COVID-19 at ICIQ, a total of 50 people is now the maximum capacity allowed in the Auditorium, so the Thesis Defense will be finally held in the Auditorium as well as through ZOOM platform too.

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