title: A general route toward the synthesis of the cladiellin skeleton utilizing a SmI2-mediated cyclization.
abstract: An efficient synthesis of the cladiellin skeleton is reported utilizing methods that were previously developed in this laboratory. The approach is based on a SmI(2)-mediated cyclization reaction for the construction of the oxacyclononane unit. A [4 + 3] annulation strategy was used to create the octahydroisobenzofuran moiety. This route provides the cladiellin skeleton in only 14 steps without the use of protecting groups. The present approach also enabled the synthesis of the 3,7-diastereomer of the natural product polyanthellin A.
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA. gmolandr@sas.upenn.edu
authors.forename: Gary A
authors.initials: GA
authors.lastname: Molander
authors.forename: Barbara
authors.initials: B
authors.lastname: Czakó
authors.forename: David J
authors.initials: DJ
authors.lastname: St Jean
mesh_terms: D000475:Alkenes / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D004224:Diterpenes / Q000737:chemistry; D007455:Iodine / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D004224:Diterpenes; D007783:Lactones; D013256:Steroids; C506145:cladiellin A; C476739:polyanthellin A; D007455:Iodine