title: Toward the total synthesis of (±)-andrastin C.
abstract: An efficient approach to generate a fully functionalized cyclopenta[a]phenanthrene 34, the basic carbon framework of andrastin C (1c), is described. The present synthetic route features a stereoselective intramolecular Diels-Alder reaction of triene 12 and an intramolecular carbonyl ene reaction of 3-phenanthrenyl-2-(methoxymethoxy)propanal 31.
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan.
authors.forename: Rei
authors.initials: R
authors.lastname: Okamoto
authors.forename: Kazutaka
authors.initials: K
authors.lastname: Takeda
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Tokuyama
authors.forename: Masataka
authors.initials: M
authors.lastname: Ihara
authors.forename: Masahiro
authors.initials: M
authors.lastname: Toyota
mesh_terms: D000730:Androstadienes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000730:Androstadienes; D010616:Phenanthrenes; C100397:andrastin C