title: Cobalt- versus ruthenium-catalyzed Alder-ene reaction for the synthesis of credneramide A and B.
abstract: The first synthesis of the natural products credneramide A and B was accomplished by utilizing Alder-ene reactions between a terminal alkene and an internal alkyne to generate the rather uncommon 1,4-diene substructure of these compounds. Moreover, two different short linear sequences toward these targets are evaluated using either a cobalt-catalyzed Alder-ene reaction of 1-chloropent-1-yne or a ruthenium-catalyzed Alder-ene reaction of 1-trimethylsilyl-1-pentyne with 5-hexenoic acid derivatives in the key step transformation. In addition, saponification of the primary Alder-ene product derived from the cobalt-catalyzed Alder-ene reaction led to credneric acid, the biological precursor of both natural products.
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse 35043 Marburg, Germany.
authors.forename: Florian
authors.initials: F
authors.lastname: Erver
authors.forename: Gerhard
authors.initials: G
authors.lastname: Hilt
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010627:Phenethylamines / Q000138:chemical synthesis* / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry*
chemical_list: D000588:Amines; D005227:Fatty Acids; D010627:Phenethylamines; C570751:credneramide A; C570752:credneramide B; D003035:Cobalt; D012428:Ruthenium