RT Journal Article
T1 Epi-, epoxy- and C2-modified bengamides: Synthesis and biological Evaluation
A1 Sarabia-García, Francisco Ramón
A1 Martín-Gálvez, Francisca
A1 García-Ruiz, Cristina
A1 Sánchez-Ruiz, Antonio
A1 Vivar García, Carlos
K1 Esponjas
AB 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.
PB ACS
YR 2013
FD 2013
LK https://hdl.handle.net/10630/34592
UL https://hdl.handle.net/10630/34592
LA eng
NO 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
NO This work was financially supported by Ministerio de Economía y Competitividad (ref CTQ2010-16933), Junta de Andalucía(FQM-03329), and fellowships from Junta de Andalucía (F.M.-G.) and Ministerio de Ciencia e Innovación (C.G.-R.). We thank Dr. J. I. Trujillo (St. Louis, MO) for assistance in the preparation of this manuscript. We thank Unidad de Espectroscopía de Masas de la Universidad de Granada for exact mass spectroscopic assistance
DS RIUMA. Repositorio Institucional de la Universidad de Málaga
RD 23 ene 2026