title: Domino Synthesis of Embelin Derivatives with Antibacterial Activity.
abstract: A series of dihydropyran embelin derivatives was synthesized through a direct and highly efficient approach based on a domino Knoevenagel intramolecular hetero-Diels-Alder reaction from natural embelin (1), using unsaturated aldehydes in the presence of organocatalysts such as ethylendiamine diacetate or l-proline. The aliphatic aldehydes yielded exclusively trans adducts, while mixtures of trans and cis isomers were found in reactions with aromatic aldehydes, with the cis form always predominating. Some of the compounds obtained were active and selective against Gram-positive bacteria, including multiresistant Staphylococcus aureus clinical isolates.
authors.affiliation: Instituto Universitario de Bio-Orgánica Antonio González (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna , Avenida Astrofísico Francisco Sánchez No. 2, 38206, La Laguna, Tenerife, Spain.
authors.forename: Rosalyn
authors.initials: R
authors.lastname: Peña
authors.affiliation: Instituto Universitario de Bio-Orgánica Antonio González (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna , Avenida Astrofísico Francisco Sánchez No. 2, 38206, La Laguna, Tenerife, Spain.
authors.forename: Pedro
authors.initials: P
authors.lastname: Martín
authors.affiliation: Instituto de Biotecnología-Instituto de Ciencias Básicas, Universidad Nacional de San Juan , Avenida Libertador General San Martín 1109 (O), CP 5400, San Juan, Argentina.
authors.forename: Gabriela E
authors.initials: GE
authors.lastname: Feresin
authors.affiliation: Instituto de Biotecnología-Instituto de Ciencias Básicas, Universidad Nacional de San Juan , Avenida Libertador General San Martín 1109 (O), CP 5400, San Juan, Argentina.
authors.forename: Alejandro
authors.initials: A
authors.lastname: Tapia
authors.affiliation: Unidad de Investigación, Hospital Universitario Nuestra Señora de Candelaria , Carretera del Rosario 145, 38010, Santa Cruz de Tenerife, Spain.
authors.forename: Félix
authors.initials: F
authors.lastname: Machín
authors.affiliation: Instituto Universitario de Bio-Orgánica Antonio González (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna , Avenida Astrofísico Francisco Sánchez No. 2, 38206, La Laguna, Tenerife, Spain.
authors.forename: Ana
authors.initials: A
authors.lastname: Estévez-Braun
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D006094:Gram-Positive Bacteria / Q000187:drug effects; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry; D013211:Staphylococcus aureus / Q000187:drug effects*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000900:Anti-Bacterial Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D016227:Benzoquinones; D011392:Proline; C010945:embelin