?url_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&rft.relation=http%3A%2F%2Fd-scholarship-dev.library.pitt.edu%2F6256%2F&rft.title=The+Synthesis+of+Oxazole-containing+Natural+Products&rft.creator=Graham%2C+Thomas+H.&rft.description=The+first+section+describes+the+synthesis+of+the+C1'+to+C11'+side+chain+of+leucascandrolide+A.+The+key+step+of+the+synthesis+is+a+modified+Robinson-Gabriel+synthesis+of+the+oxazole.+The+C1'+to+C11'+side+chain+was+constructed+in+9+steps+and+7%25+overall+yield.The+second+section+describes+the+synthesis+of+2-alkynyl+oxazoles+and+subsequent+transformations+into+a+variety+of+useful+motifs.+The+conjugate+addition+of+nucleophiles+to+2-alkynyl+oxazoles+under+basic+conditions+affords+vinyl+ethers%2C+vinyl+thioethers+and+enamines.+The+addition+of+ethanedithiol+affords+dithiolanes+that+can+be+transformed+into+ethyl+thioesters+and+ketones.+Nucleophilic+additions+of+thiols+to+2-alkynyl+oxazolines+affords+oxazoline+thioethers.+Additions+of+halides+under+acidic+conditions+stereoselectively+affords+vinyl+halides+that+can+be+further+transformed+by+Sonogashira+cross-coupling+reactions.The+third+section+describes+the+synthesis+of+(-)-disorazole+C1+and+analogs.+The+macrocycle+was+constructed+with+minimal+protecting+group+manipulations%2C+using+mild+esterification+and+Sonogashira+cross-coupling+reactions.+The+convergent+synthesis+of+disorazole+C1+allowed+for+the+synthesis+of+additional+analogs.+These+analogs+include+the+C14-t-butyl+and+C17-18-cyclopropane+derivatives.+Results+from+preliminary+biological+evaluations+of+synthetic+intermediates%2C+analogs+and+derivatives+are+also+discussed.&rft.date=2006-06-01&rft.type=University+of+Pittsburgh+ETD&rft.type=PeerReviewed&rft.format=application%2Fpdf&rft.language=en&rft.identifier=http%3A%2F%2Fd-scholarship-dev.library.pitt.edu%2F6256%2F1%2Fgrahamth_etd2006.pdf&rft.identifier=++Graham%2C+Thomas+H.++(2006)+The+Synthesis+of+Oxazole-containing+Natural+Products.++Doctoral+Dissertation%2C+University+of+Pittsburgh.++++(Unpublished)++