?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%2F12266%2F&rft.title=Synthetic+Studies+on+Cycloclavine%2C+Cyclopiazonic+Acid%2C+and+Other+Biologically+Active+Indole-Containing+Compounds&rft.creator=Petronijevic%2C+Filip&rft.description=The+first+section+of+this+dissertation+describes+the+synthesis+of+five+indole-containing+compounds+used+in+the+BoNT+LC+(botulinum+neurotoxin+light+chain)+SAR+analysis.+Our+approach+employs+a+Pd(II)-catalyzed+cyclization+for+the+formation+of+indole+rings%2C+which+are+subsequently+converted+to+the+corresponding+amidines+or+imidazolines.%0D%0AThe+second+section+describes+the+extension+of+the+indole+synthesis+methodology+through+a+microwave+assisted+IMDAF+(intramolecular+Diels-Alder+furan)+reaction.+This+protocol+allows+for+a+convergent+and+rapid+preparation+of+4-mono-+and+3%2C4-disubstituted+indoles.+This+cascade+process+is+quite+tolerant+of+functional+groups+and+associated+substitution+patterns.%0D%0AThe+third+part+we+describes+novel+routes+to+the+naturally+occurring+indole+alkaloid+cycloclavine+and+its+unnatural+C(5)-epimer.+Key+features+include+the+rapid+construction+of+the+heterocyclic+core+segments+by+two+Diels-Alder+reactions.+An+indole+annulation+was+accomplished+by+a+late-stage+IMDAF+reaction%2C+while+the+cyclopropa%5Bc%5Dindoline+core+of+cycloclavine+was+derived+through+a+stereoselective+intramolecular+%5B4%2B2%5D+cycloaddition+of+a+methylenecyclopropane.%0D%0AThe+forth+section+describes+an+approach+towards+the+total+synthesis+of+cyclopiazonic+acid.+A+promising+route+to+this+alkaloid+was+established%2C+including+a+rapid+construction+of+the+tricyclic+indole-containing+core+and+a+stereoselective+pyrrolidinone+ring+formation.+%0D%0A&rft.date=2012-10-02&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%2F12266%2F1%2FFilip_Petronijevic.pdf&rft.identifier=++Petronijevic%2C+Filip++(2012)+Synthetic+Studies+on+Cycloclavine%2C+Cyclopiazonic+Acid%2C+and+Other+Biologically+Active+Indole-Containing+Compounds.++Doctoral+Dissertation%2C+University+of+Pittsburgh.++++(Unpublished)++