RT Journal Article
T1 Exploring the chemistry of epoxy amides for the synthesis of the 2"-epi-diazepanone core of liposidomycins and caprazamycins
A1 Sarabia-García, Francisco Ramón
A1 Vivar García, Carlos
A1 García-Ruiz, Cristina
A1 Martín Ortiz, Laura
A1 Romero-Carrasco, Antonio
K1 Antibióticos
AB New synthetic strategies have been explored for the synthesis of the structural core of liposidomycins and caprazamycins, an intriguing class of complex nucleoside-type antibiotics. This structural core is comprised of a cyclic diazepanone system linked to an uridyl fragment. The various synthetic approaches have in common that they originate from an epoxy amide derived from uridine, obtained via reaction of uridyl aldehyde 19 with an amide-stabilized sulfur ylide. Two different strategies were shown to be efficient in constructing the diazepanone ring system: (a) a reductive amination of an epoxy aldehyde with N methylamine with subsequent intramolecular oxirane ring opening and (b) a carbene insertion reaction of an acyclic diazoamine precursor.
PB ACS
YR 2012
FD 2012
LK https://hdl.handle.net/10630/34589
UL https://hdl.handle.net/10630/34589
LA eng
NO Sarabia, F.; Vivar-García; C.; García-Ruiz, C.; Martín-Ortiz, L.; Romero-Carrasco, A. Exploring the chemistry of epoxy amides for the synthesis of the 2"-epi-diazepanone core of liposidomycins and caprazamycins
NO This work was financially supported by the Dirección General de Investigación y Científica Técnica (ref CTQ2010-16933)and Consejería de Educación y Ciencia of Junta de Andalucía (FQM-03329). C.G.-R. thanks the Ministerio de Educación y Ciencia for a fellowship. We thank Dr. J. I. Trujillo 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 19 ene 2026