title: Enantioselective total synthesis of (+)-ophiobolin A.
abstract: The enantioselective total synthesis of (+)-ophiobolin A is described. This total synthesis features the construction of the spiro CD ring of (+)-ophiobolin A through a stereoselective intramolecular Hosomi-Sakurai cyclization reaction, the joining of the A ring to the CD ring by using a reaction reported by Utimoto, and the construction of the ophiobolin eight-membered carbocyclic ring through ring-closing metathesis (RCM), which was performed for the first time in this study. This successful RCM reaction required the use of a substrate that contained either a benzyloxy or a methoxymethoxy group at the C5 position and either an isopropenyl group or its hydroxylated form at the C6 position.
authors: Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.
authors: Kazuhiro
authors: K
authors: Tsuna
authors: Naoyoshi
authors: N
authors: Noguchi
authors: Masahisa
authors: M
authors: Nakada
mesh_terms: D003500:Cyclization; D015394:Molecular Structure; D054830:Sesterterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D054830:Sesterterpenes; C040764:ophiobolin A