title: Stereoselective cascade reactions that incorporate a 7-exo acyl radical cyclization.
abstract: [reaction: see text] Radical cascades that feature a 7-exo acyl radical cyclization followed by a 6-exo or 5-exo alkyl radical cyclization proceed with very good yields and diastereoselectivities. Two stereocenters are created by the reaction, and a single isomeric product was obtained from each of the five substrates examined. The relative configurations of the products are consistent with cyclizations occurring via chairlike or pseudochairlike transition states.
authors.affiliation: Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, USA.
authors.forename: Seth W
authors.initials: SW
authors.lastname: Grant
authors.forename: Koudi
authors.initials: K
authors.lastname: Zhu
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhang
authors.forename: Steven L
authors.initials: SL
authors.lastname: Castle
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000473:Alkanes / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000473:Alkanes; D011083:Polycyclic Compounds; C435307:lyconadin A