title: Total synthesis of nostodione A, a cyanobacterial metabolite.
abstract: The first total synthesis of the mitotic spindle poison nostodione A is described. The inherent oxidative sensitivity of indoles is utilized for a late introduction of a second carbonyl to the cyclopent[b]indole-2-one system. The tricyclic system is prepared from indole-3-acetic acid and O-silylated 4-ethynylphenol, using a stereoselective intramolecular reductive Heck cyclization as the key transformation.
authors.affiliation: Department of Chemical and Biological Engineering/Organic Chemistry, Chalmers University of Technology, SE-412 96 Gothenburg, Sweden.
authors.forename: Andreas
authors.initials: A
authors.lastname: Ekebergh
authors.forename: Anna
authors.initials: A
authors.lastname: Börje
authors.forename: Jerker
authors.initials: J
authors.lastname: Mårtensson
mesh_terms: D000458:Cyanobacteria / Q000378:metabolism; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; C541082:nostodione A