title: Step-economical synthesis of the marine ascidian antibiotics cadiolide A, B, and D.
abstract: A concise, modular and efficient synthesis of the title natural products is reported. Prominent steps include (i) one-pot assembly of a key β-aryl-α-benzoylbutenolide building block by regiocontrolled "click-unclick" oxazole-ynone Diels-Alder cycloaddition/cycloreversion and ensuing 2-alkoxyfuran hydrolysis and (ii) a protecting group-free vinylogous Knoevenagel condensation enabling rapid access to cadiolides A, B, and D from a common precursor.
authors.affiliation: Département de Chimie, Université Laval, Pavillon Alexandre-Vachon, 1045 Avenue de la Médecine, Quebec City, Quebec G1V 0A6, Canada.
authors.forename: John
authors.initials: J
authors.lastname: Boukouvalas
authors.affiliation: Département de Chimie, Université Laval, Pavillon Alexandre-Vachon, 1045 Avenue de la Médecine, Quebec City, Quebec G1V 0A6, Canada.
authors.forename: Charles
authors.initials: C
authors.lastname: Thibault
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D059001:Aquatic Organisms / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D014561:Urochordata / Q000737:chemistry*
chemical_list: D000900:Anti-Bacterial Agents; C000599604:cadiolide A; C000599605:cadiolide B; C000599606:cadiolide D; D015107:4-Butyrolactone