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  • Title: Epi-, epoxy-, and C2-modified bengamides: synthesis and biological evaluation.
    Author: Sarabia F, Martín-Gálvez F, García-Ruiz C, Sánchez-Ruiz A, Vivar-García C.
    Journal: J Org Chem; 2013 Jun 07; 78(11):5239-53. PubMed ID: 23647394.
    Abstract:
    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.
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