Mercuric acetate-mediated annulation of homopropargylic alcohols having thioether substituent. A general route for the synthesis of tetrasubstituted furans from propargylic dithioacetals
Journal
Tetrahedron Letters
Journal Volume
50
Journal Issue
26
Pages
3263-3265
Date Issued
2009
Author(s)
Chen C.-W
Abstract
Treatment 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.
Other Subjects
acetal derivative; alcohol derivative; aldehyde; alkyl group; furan; iodine; mercury; sulfide; annulation reaction; article; cyclization; diastereoisomer; stereochemistry; substitution reaction; synthesis
Type
journal article