{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T09:13:55Z","timestamp":1792487635319,"version":"4.5.0"},"reference-count":79,"publisher":"American Chemical Society (ACS)","issue":"20","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Org. Chem."],"published-print":{"date-parts":[[2008,10,17]]},"DOI":"10.1021\/jo8015924","type":"journal-article","created":{"date-parts":[[2008,9,18]],"date-time":"2008-09-18T08:02:34Z","timestamp":1221724954000},"page":"8109-8112","source":"Crossref","is-referenced-by-count":67,"title":["General, Regiodefined Access to \u03b1-Substituted Butenolides through Metal\u2212Halogen Exchange of 3-Bromo-2-silyloxyfurans. Efficient Synthesis of an Anti-inflammatory Gorgonian Lipid"],"prefix":"10.1021","volume":"73","author":[{"given":"John","family":"Boukouvalas","sequence":"first","affiliation":[{"name":"D\u00e9partement de Chimie, Universit\u00e9 Laval, Quebec City, Quebec G1K 7P4, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Richard P.","family":"Loach","sequence":"additional","affiliation":[{"name":"D\u00e9partement de Chimie, Universit\u00e9 Laval, Quebec City, Quebec G1K 7P4, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2008,9,18]]},"reference":[{"key":"ref1\/cit1a","doi-asserted-by":"crossref","first-page":"4228","DOI":"10.1016\/j.bmcl.2006.05.077","volume":"16","author":"Shults E. E.","year":"2006","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref1\/cit1b","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1038\/sj.bjp.0706944","volume":"150","author":"Koo K. A.","year":"2007","journal-title":"Br. J. Pharmacol."},{"key":"ref2\/cit2","unstructured":"Kaushik, M. P.; Thavaselvam, D.; Nivsarkar, M.; Acharya, B. N.; Prasanna, S.; Sekhar,K. PCT Int. Appl. (2007) WO 2007039915 (CA:2007,146, 408201)."},{"key":"ref3\/cit3","doi-asserted-by":"crossref","first-page":"1369","DOI":"10.1021\/np0301487","volume":"66","author":"Son J. K.","year":"2003","journal-title":"J. Nat. Prod."},{"key":"ref4\/cit4","doi-asserted-by":"crossref","first-page":"1172","DOI":"10.1248\/cpb.31.1172","volume":"31","author":"Kikuchi H.","year":"1983","journal-title":"Chem. Pharm. Bull."},{"key":"ref5\/cit5a","doi-asserted-by":"crossref","first-page":"7897","DOI":"10.1016\/S0040-4039(00)78379-1","volume":"48","author":"Boukouvalas J.","year":"1994","journal-title":"Tetrahedron Lett."},{"key":"ref5\/cit5b","doi-asserted-by":"crossref","first-page":"641","DOI":"10.1139\/v97-078","volume":"75","author":"De la Cruz R. A.","year":"1997","journal-title":"Can. J. Chem."},{"key":"ref5\/cit5c","doi-asserted-by":"crossref","first-page":"12387","DOI":"10.1016\/S0040-4020(99)00721-8","volume":"55","author":"Bella M.","year":"1999","journal-title":"Tetrahedron"},{"key":"ref5\/cit5d","doi-asserted-by":"crossref","first-page":"52","DOI":"10.1021\/ja9930059","volume":"122","author":"Monovich L. G.","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5e","first-page":"1114","author":"Goeller F.","year":"2001","journal-title":"Synthesis"},{"key":"ref5\/cit5f","doi-asserted-by":"crossref","first-page":"6323","DOI":"10.1016\/S0040-4020(02)00631-2","volume":"58","author":"Reichelt A.","year":"2002","journal-title":"Tetrahedron"},{"key":"ref5\/cit5g","doi-asserted-by":"crossref","first-page":"343","DOI":"10.1055\/s-2004-837220","author":"Boukouvalas J.","year":"2005","journal-title":"Synlett"},{"key":"ref5\/cit5h","doi-asserted-by":"crossref","first-page":"543","DOI":"10.1021\/ol053054s","volume":"8","author":"Huang Q.","year":"2006","journal-title":"Org. Lett."},{"key":"ref5\/cit5i","doi-asserted-by":"crossref","first-page":"151","DOI":"10.1039\/B613544G","volume":"5","author":"Nagase R.","year":"2007","journal-title":"Org. Biomol. Chem."},{"key":"ref5\/cit5j","doi-asserted-by":"crossref","first-page":"7747","DOI":"10.1016\/j.tetlet.2007.09.033","volume":"48","author":"Boukouvalas J.","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"ref6\/cit6a","doi-asserted-by":"crossref","first-page":"4501","DOI":"10.1021\/jo020161g","volume":"67","author":"Taber D. F.","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref6\/cit6b","doi-asserted-by":"crossref","first-page":"2362","DOI":"10.1002\/ejoc.200500928","author":"Shiina J.","year":"2006","journal-title":"Eur. J. Org. Chem."},{"key":"ref6\/cit6c","first-page":"2198","author":"Haval K. P.","year":"2007","journal-title":"Synthesis"},{"key":"ref7\/cit7a","doi-asserted-by":"crossref","first-page":"214","DOI":"10.1002\/ps.1147","volume":"62","author":"Barbosa L. C. A.","year":"2006","journal-title":"Pest Manage. Sci."},{"key":"ref7\/cit7b","doi-asserted-by":"crossref","first-page":"8562","DOI":"10.1021\/jf072120x","volume":"55","author":"Barbosa L. C. A.","year":"2007","journal-title":"J. Agric. Food Chem."},{"key":"ref7\/cit7c","doi-asserted-by":"crossref","first-page":"2321","DOI":"10.1021\/jf072964g","volume":"56","author":"Teixeira R. R.","year":"2008","journal-title":"J. Agric. Food Chem."},{"key":"ref8\/cit8","unstructured":"Review:"},{"key":"ref8\/cit8a","doi-asserted-by":"crossref","first-page":"287","DOI":"10.1039\/co9940100287","volume":"1","author":"Knight D. W.","year":"1994","journal-title":"Contemp. Org. Synth."},{"key":"ref9\/cit9a","doi-asserted-by":"crossref","first-page":"1888","DOI":"10.1021\/ja00112a004","volume":"117","author":"Trost B. M.","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"ref9\/cit9b","doi-asserted-by":"crossref","first-page":"367","DOI":"10.1021\/jo9618740","volume":"62","author":"Marshall J. A.","year":"1997","journal-title":"J. Org. Chem."},{"key":"ref9\/cit9c","doi-asserted-by":"crossref","first-page":"989","DOI":"10.1016\/S0040-4039(98)02464-2","volume":"40","author":"Gabriele B.","year":"1999","journal-title":"Tetrahedron Lett."},{"key":"ref9\/cit9d","doi-asserted-by":"crossref","first-page":"1241","DOI":"10.3987\/COM-99-S138","volume":"52","author":"Liao B.","year":"2000","journal-title":"Heterocycles"},{"key":"ref9\/cit9e","doi-asserted-by":"crossref","first-page":"8571","DOI":"10.1021\/jo0350615","volume":"68","author":"Yoneda E.","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref10\/cit10a","doi-asserted-by":"crossref","first-page":"3657","DOI":"10.1016\/S0040-4039(01)00534-2","volume":"42","author":"Pashkovsky F. S.","year":"2001","journal-title":"Tetrahedron Lett."},{"key":"ref10\/cit10b","doi-asserted-by":"crossref","first-page":"3165","DOI":"10.1002\/1099-0690(200108)2001:16<3165::AID-EJOC3165>3.0.CO;2-6","author":"Arcadi A.","year":"2001","journal-title":"Eur. J. Org. Chem."},{"key":"ref10\/cit10c","doi-asserted-by":"crossref","first-page":"4429","DOI":"10.1016\/S0040-4020(01)00331-3","volume":"57","author":"Bella M.","year":"2001","journal-title":"Tetrahedron"},{"key":"ref10\/cit10d","doi-asserted-by":"crossref","first-page":"9117","DOI":"10.1016\/S0040-4020(02)00995-X","volume":"58","author":"Carter N. B.","year":"2002","journal-title":"Tetrahedron"},{"key":"ref10\/cit10e","doi-asserted-by":"crossref","first-page":"1983","DOI":"10.1016\/j.tet.2004.01.004","volume":"60","author":"Hagiwara H.","year":"2004","journal-title":"Tetrahedron"},{"key":"ref10\/cit10f","first-page":"1575","author":"Ce\u00f1al J. P.","year":"2005","journal-title":"Synlett"},{"key":"ref11\/cit11","doi-asserted-by":"crossref","first-page":"4377","DOI":"10.1016\/j.tetlet.2006.04.097","volume":"47","author":"Jones S.","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"ref12\/cit12a","doi-asserted-by":"crossref","first-page":"1391","DOI":"10.1016\/S0040-4039(00)84267-7","volume":"27","author":"N\u00e4sman J. H.","year":"1986","journal-title":"Tetrahedron Lett."},{"key":"ref12\/cit12b","first-page":"396","volume":"8","author":"N\u00e4sman J. H.","year":"1993","journal-title":"Org. Synth."},{"key":"ref13\/cit13a","doi-asserted-by":"crossref","first-page":"1511","DOI":"10.1055\/s-2006-944202","author":"Boukouvalas J.","year":"2006","journal-title":"Synlett"},{"key":"ref13\/cit13b","doi-asserted-by":"crossref","first-page":"6670","DOI":"10.1021\/jo0610154","volume":"71","author":"Boukouvalas J.","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref14\/cit14","unstructured":"Prepared in two steps from the parent butenolide (82% overall yield); see the Supporting Information of ref13bfor experimental details."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"1199","DOI":"10.1016\/S0040-4020(01)86685-0","volume":"46","author":"Bock I.","year":"1990","journal-title":"Tetrahedron"},{"key":"ref16\/cit16","unstructured":"For a similar observation on the use of DMPU in a related reaction, see:"},{"key":"ref16\/cit16a","first-page":"1324","author":"Xin Z.","year":"2000","journal-title":"Synlett"},{"key":"ref17\/cit17","unstructured":"The precise mechanism of metal\u2212halogen exchange reactions has yet to be settled; for recent studies see:"},{"key":"ref17\/cit17a","doi-asserted-by":"crossref","first-page":"6021","DOI":"10.1021\/om9705721","volume":"16","author":"Jedlicka B.","year":"1997","journal-title":"Organometallics"},{"key":"ref17\/cit17b","doi-asserted-by":"crossref","first-page":"313\u2212316","DOI":"10.1021\/ol027307i","volume":"5","author":"Hoffmann R. W.","year":"2003","journal-title":"Org. Lett."},{"key":"ref18\/cit18a","first-page":"986","author":"Kv\u00ed\u00e8ala J.","year":"1997","journal-title":"Synlett"},{"key":"ref18\/cit18b","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1016\/S0022-1139(99)00235-3","volume":"102","author":"Paleta O.","year":"2000","journal-title":"J. Fluorine Chem."},{"key":"ref18\/cit18c","doi-asserted-by":"crossref","first-page":"2809","DOI":"10.1039\/B209079A","author":"Motherwell W. B.","year":"2002","journal-title":"J. Chem. Soc., Perkin Trans. 1"},{"key":"ref19\/cit19a","doi-asserted-by":"crossref","first-page":"4831","DOI":"10.1021\/ol0618611","volume":"8","author":"Aquino M.","year":"2006","journal-title":"Org. Lett."},{"key":"ref19\/cit19b","doi-asserted-by":"crossref","first-page":"6305","DOI":"10.1021\/jo070666c","volume":"72","author":"Patil S. N.","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref19\/cit19c","doi-asserted-by":"crossref","first-page":"1058","DOI":"10.1246\/cl.2007.1058","volume":"36","author":"Li C.","year":"2007","journal-title":"Chem. Lett."},{"key":"ref19\/cit19d","doi-asserted-by":"crossref","first-page":"2021","DOI":"10.1021\/jo7025405","volume":"73","author":"Margaros I.","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref19\/cit19e","doi-asserted-by":"crossref","first-page":"4476","DOI":"10.1021\/jo702762u","volume":"73","author":"Patil S. N.","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref20\/cit20a","first-page":"1286","author":"Sorg A.","year":"2005","journal-title":"Synlett"},{"key":"ref20\/cit20b","first-page":"538","author":"Mathews C. J.","year":"2005","journal-title":"Synlett"},{"key":"ref20\/cit20c","doi-asserted-by":"crossref","first-page":"12457","DOI":"10.1016\/S0040-4020(01)89551-X","volume":"50","author":"Ochoa de Echag\u00fcen C.","year":"1994","journal-title":"Tetrahedron"},{"key":"ref21\/cit21","doi-asserted-by":"crossref","first-page":"2456","DOI":"10.1021\/ja025604c","volume":"124","author":"Movassaghi M.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref22\/cit22","unstructured":"For the oxyfunctionalization of 2-silyloxyfurans and related compounds, see:"},{"key":"ref22\/cit22a","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1055\/s-1998-1574","author":"Boukouvalas J.","year":"1998","journal-title":"Synlett"},{"key":"ref22\/cit22b","doi-asserted-by":"crossref","first-page":"228","DOI":"10.1021\/jo972208h","volume":"63","author":"Boukouvalas J.","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref22\/cit22c","doi-asserted-by":"crossref","first-page":"7025","DOI":"10.1016\/S0040-4039(98)01471-3","volume":"39","author":"Boukouvalas J.","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"ref22\/cit22d","doi-asserted-by":"crossref","first-page":"3301","DOI":"10.1055\/s-2005-918475","author":"Marcos I. S.","year":"2005","journal-title":"Synthesis"},{"key":"ref22\/cit22e","doi-asserted-by":"crossref","first-page":"2480","DOI":"10.1055\/s-2006-949641","author":"Boukouvalas J.","year":"2006","journal-title":"Synlett"},{"key":"ref22\/cit22f","doi-asserted-by":"crossref","first-page":"3198","DOI":"10.1055\/s-2007-992376","author":"Boukouvalas J.","year":"2007","journal-title":"Synlett"},{"key":"ref23\/cit23","unstructured":"For some recent synthetic applications of vinylogous reactions of 2-silyloxyfurans with carbon electrophiles, see:"},{"key":"ref23\/cit23a","doi-asserted-by":"crossref","first-page":"895","DOI":"10.1021\/ar950230w","volume":"35","author":"Martin S. F.","year":"2002","journal-title":"Acc. Chem. Res."},{"key":"ref23\/cit23b","doi-asserted-by":"crossref","first-page":"3989","DOI":"10.1021\/ol051483k","volume":"7","author":"Hanessian S.","year":"2005","journal-title":"Org. Lett."},{"key":"ref23\/cit23c","doi-asserted-by":"crossref","first-page":"545","DOI":"10.1021\/ol0478281","volume":"7","author":"Vaz B.","year":"2005","journal-title":"Org. Lett."},{"key":"ref23\/cit23d","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1016\/j.tetlet.2005.10.163","volume":"47","author":"Rosso G. B.","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"ref23\/cit23e","doi-asserted-by":"crossref","first-page":"7230","DOI":"10.1002\/anie.200603496","volume":"45","author":"Carswell E. L.","year":"2006","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref23\/cit23f","doi-asserted-by":"crossref","first-page":"597","DOI":"10.1021\/ol0527328","volume":"8","author":"Robichaud J.","year":"2006","journal-title":"Org. Lett."},{"key":"ref23\/cit23g","doi-asserted-by":"crossref","first-page":"3705","DOI":"10.1021\/ol061284g","volume":"8","author":"Maulide N.","year":"2006","journal-title":"Org. Lett."},{"key":"ref23\/cit23h","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1021\/ja061146m","volume":"128","author":"Catino A. J.","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref23\/cit23i","doi-asserted-by":"crossref","first-page":"11032","DOI":"10.1021\/ja063532+","volume":"128","author":"Boeckman R. K.","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref23\/cit23j","doi-asserted-by":"crossref","first-page":"219","DOI":"10.1055\/s-2007-968004","author":"Boukouvalas J.","year":"2007","journal-title":"Synlett"},{"key":"ref23\/cit23k","doi-asserted-by":"crossref","first-page":"4698","DOI":"10.1002\/anie.200701520","volume":"46","author":"Evans D. A.","year":"2007","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref24\/cit24a","doi-asserted-by":"crossref","first-page":"2377","DOI":"10.1002\/cber.19911241036","volume":"124","author":"Adam W.","year":"1991","journal-title":"Chem. Ber."},{"key":"ref24\/cit24b","doi-asserted-by":"crossref","first-page":"91","DOI":"10.15227\/orgsyn.074.0091","volume":"74","author":"Murray R. W.","year":"1997","journal-title":"Org. Synth."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo8015924","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,8]],"date-time":"2023-03-08T21:36:20Z","timestamp":1678311380000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jo8015924"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,9,18]]},"references-count":79,"journal-issue":{"issue":"20","published-print":{"date-parts":[[2008,10,17]]}},"alternative-id":["10.1021\/jo8015924"],"URL":"https:\/\/doi.org\/10.1021\/jo8015924","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2008,9,18]]}}}