Mercuric acetate-mediated annulation of homopropargylic alcohols having thioether substituent. A general route for the synthesis of tetrasubstituted furans from propargylic dithioacetals

Chen C.-WTIEN-YAU LUH2022-12-142022-12-14200900404039https://www.scopus.com/inward/record.uri?eid=2-s2.0-65549085332&doi=10.1016%2fj.tetlet.2009.02.043&partnerID=40&md5=54b216b1e65b82629e5bff099f5a7ab2https://scholars.lib.ntu.edu.tw/handle/123456789/626303Treatment of an alkyl-substituted propargylic dithioacetal with nBuLi followed by an aldehyde furnishes thio-substituted homopropargylic alcohol 7 which undergoes annulation in the presence of two equivalents of mercury acetate to give the corresponding mercurio-substituted furan 12. Reaction of 12 with iodine gives iodofuran in moderate to good yield. © 2009 Elsevier Ltd. All rights reserved.[SDGs]SDG6acetal derivative; alcohol derivative; aldehyde; alkyl group; furan; iodine; mercury; sulfide; annulation reaction; article; cyclization; diastereoisomer; stereochemistry; substitution reaction; synthesisMercuric acetate-mediated annulation of homopropargylic alcohols having thioether substituent. A general route for the synthesis of tetrasubstituted furans from propargylic dithioacetalsjournal article10.1016/j.tetlet.2009.02.0432-s2.0-65549085332