eprintid: 18738 rev_number: 18 userid: 1418 dir: disk0/00/01/87/38 datestamp: 2013-05-28 15:16:10 lastmod: 2019-02-02 15:58:42 status_changed: 2013-05-28 15:16:10 type: article metadata_visibility: show item_issues_count: 0 eprint_status: archive creators_name: Yang, F creators_name: Newsome, JJ creators_name: Curran, DP creators_email: creators_email: creators_email: curran@pitt.edu creators_id: creators_id: creators_id: CURRAN title: Structure assignment of lagunapyrone B by fluorous mixture synthesis of four candidate stereoisomers ispublished: pub divisions: sch_as_chemistry full_text_status: public abstract: Techniques of fluorous mixture synthesis have been used to make four candidate stereoisomers for the natural product lagunapyrone B. A quasiracemic mixture of vinyl iodides whose component configurations at C19-21 were encoded by fluorous silyl groups was fused to a central fragment by a Negishi coupling. A separate quasiracemic mixture of pyrone fragments whose component configurations at C6,7 were also encoded by fluorous silyl groups was synthesized and demixed. Stille coupling of the resulting pure quasienantiomers with the quasiracemic mixture provided two quasi-diastereomeric samples, which were demixed and detagged to provide all four lagunapyrone B stereoisomers. Lagunapyrone was assigned the 6R,7S,19S,20S,21R configuration by comparison of optical rotations. © 2006 American Chemical Society. date: 2006-11-01 date_type: published publication: Journal of the American Chemical Society volume: 128 number: 43 pagerange: 14200 - 14205 refereed: TRUE issn: 0002-7863 id_number: 10.1021/ja064812s pmid: 17061905 mesh_headings: Alkenes--chemistry mesh_headings: Molecular Structure mesh_headings: Pyrones--chemistry mesh_headings: Stereoisomerism chemical_names: Alkenes chemical_names: Pyrones chemical_names: lagunapyrone B citation: Yang, F and Newsome, JJ and Curran, DP (2006) Structure assignment of lagunapyrone B by fluorous mixture synthesis of four candidate stereoisomers. Journal of the American Chemical Society, 128 (43). 14200 - 14205. ISSN 0002-7863 document_url: http://d-scholarship-dev.library.pitt.edu/18738/1/licence.txt