title: Torsional steering controls the stereoselectivity of epoxidation in the guanacastepene a synthesis.
abstract: [reaction: see text] The stereoselectivity of the key epoxidation step in the synthesis of guanacastepene A is shown to be controlled by torsional steering. In this particular epoxidation reaction, the transition structure energetic difference is enhanced by the great asynchronicity of the forming C-O bonds that intensifies the torsional interactions.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
authors.forename: Paul Ha-Yeon
authors.initials: PH
authors.lastname: Cheong
authors.forename: Heedong
authors.initials: H
authors.lastname: Yun
authors.forename: Samuel J
authors.initials: SJ
authors.lastname: Danishefsky
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
mesh_terms: D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; C409194:guanacastepene