eprintid: 20619 rev_number: 16 userid: 1418 dir: disk0/00/02/06/19 datestamp: 2014-02-21 21:03:22 lastmod: 2019-02-02 15:58:54 status_changed: 2014-02-21 21:03:22 type: article metadata_visibility: show item_issues_count: 0 eprint_status: archive creators_name: Haney, BP creators_name: Curran, DP creators_email: creators_email: curran@pitt.edu creators_id: creators_id: CURRAN title: Round trip radical reactions from acyclic precursors to tricyclo[5.3.1.02,6]undecanes. A new cascade radical cyclization approach to (±)-isogymnomitrene and (±)-gymnomitrene ispublished: pub divisions: sch_as_chemistry full_text_status: public abstract: The synthesis and 'round trip radical cyclization' of 11-iodo-2,7,11- trimethyldodec-6-en-5-one are described. The round trip cyclization is a sequence of 5-exo, 6-endo, and 5-exo cyclizations in which the last radical cyclization occurs at the same carbon atom as the initial radical generation. The key second (6-endo) cyclization produces two stereoisomers, one of which cyclizes efficiently to isogymnomitrene ketone, while the other cyclizes inefficiently to gymnomitrene ketone. Efforts to influence the kinetic or thermodynamic outcome of the second cyclization were not successful, and the results are contrasted with a related cyclization of Jung and Rayle where thermodynamic control was readily established. date: 2000-04-07 date_type: published publication: Journal of Organic Chemistry volume: 65 number: 7 pagerange: 2007 - 2013 refereed: TRUE issn: 0022-3263 id_number: 10.1021/jo9914871 pmid: 10841670 mesh_headings: Bridged Compounds--chemical synthesis mesh_headings: Cyclization mesh_headings: Free Radicals--chemistry mesh_headings: Stereoisomerism chemical_names: Bridged Compounds chemical_names: Free Radicals citation: Haney, BP and Curran, DP (2000) Round trip radical reactions from acyclic precursors to tricyclo[5.3.1.02,6]undecanes. A new cascade radical cyclization approach to (±)-isogymnomitrene and (±)-gymnomitrene. Journal of Organic Chemistry, 65 (7). 2007 - 2013. ISSN 0022-3263 document_url: http://d-scholarship-dev.library.pitt.edu/20619/1/licence.txt