title: A synthesis of the ABC tricyclic core of the clionastatins serves to corroborate their proposed structures.
abstract: A synthesis of the ABC tricyclic ring system of the clionastatins, an unusual pair of highly chlorinated androstane steroids, has been accomplished. This work provides strong support for the original structural proposal. An unexpected substrate-dependent reversal in alkene chlorination diastereoselectivity was critical to success. This approach should be amenable to an eventual enantioselective synthesis of the natural products themselves.
authors.affiliation: Department of Chemistry, University of California , 1102 Natural Sciences II, Irvine, California 92697-2025, United States.
authors.forename: Samuel S
authors.initials: SS
authors.lastname: Tartakoff
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Vanderwal
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000731:Androstanes / Q000138:chemical synthesis* / Q000737:chemistry*; D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000731:Androstanes; D001688:Biological Products; C494536:clionastatin A; C494535:clionastatin B