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Epi-, epoxy- and C2-modified bengamides: Synthesis and biological Evaluation Sarabia-García, Francisco Ramón Martín-Gálvez, Francisca García-Ruiz, Cristina Sánchez-Ruiz, Antonio Vivar García, Carlos Esponjas With the objective of investigating the influence of structural modifications of the polyketide chain of the bengamides upon their antitumoral activities, we targeted the preparation of bengamide E analogues with modification of the stereochemistry at C-2 and at C-3, the substituent at the C-2 position, and the presence of oxirane rings. For the synthesis of these analogues, a new synthetic method for asymmetric epoxidation, developed in our laboratories, was employed utilizing the chiral sulfonium salts 22 and 23. In order to access 2-epi-bengamide E from these epoxy amides, a synthetic methodology, developed by Miyashita, allowed an oxirane-ring-opening reaction with a double inversion of the configuration. Alternatively, an aldol reaction provided access to the same analogue in a shorter and more efficient manner. Finally, biological evaluation of all of these bengamide E analogues demonstrated that the polyketide chain is essential for the antitumor activity of these natural products, not being amenable to structural or configurational modifications. 2024-10-10T07:31:17Z 2024-10-10T07:31:17Z 2024 2013 journal article Sarabia, F.; Martín-Gálvez, F.; García-Ruiz, C.; Sánchez-Ruiz, A.; Vivar-García, C. Epistemológica-, epoxy-, and C2-modified benjamines: Synthesis and biological evaluation. J. Org. Chem. 2013, 78, 11, 5239-5253 https://doi.org/10.1021/jo4003272 https://hdl.handle.net/10630/34592 10.1021/jo4003272 eng http://creativecommons.org/licenses/by-nc-nd/4.0/ open access Attribution-NonCommercial-NoDerivatives 4.0 Internacional ACS