title: Synthesis of (+/-)-epi-stegobinone utilizing silacyclopropanes as synthetic intermediates.
abstract: The synthesis of (+/-)-1'-epi-stegobinone has been accomplished in ten steps and 17% overall yield from a recently reported silacyclopropane-derived diol. All stereocenters of the final product were established relative to the stereochemistry of the initial silacyclopropane. This synthesis represents the first time silacyclopropane reactivity has been employed in a target-directed synthesis.
authors.affiliation: Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
authors.forename: Stacie A
authors.initials: SA
authors.lastname: Calad
authors.forename: Jelena
authors.initials: J
authors.lastname: Ciraković
authors.forename: K A
authors.initials: KA
authors.lastname: Woerpel
mesh_terms: D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D008956:Models, Chemical; D011753:Pyrones / Q000138:chemical synthesis*; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003521:Cyclopropanes; D011753:Pyrones; C101374:stegobinone; D012825:Silicon