{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Greshock TJ"],"funding":["NIGMS NIH HHS"],"pagination":["4946-7"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC2597544"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["128(15)"],"pubmed_abstract":["A new method for the preparation of indoles from readily available alpha-haloenones and alpha-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6pi-electrocyclic ring closure and subsequent oxidation to afford protected aniline 4. Upon deprotection and reductive amination, acid 5 underwent clean cyclization to N-acetylindole 6 (Ac2O, NEt3, 130 degrees C). This method has been used to construct a variety of substituted indoles that are not easily prepared by conventional indole annelation methods."],"journal":["Journal of the American Chemical Society"],"pubmed_title":["Synthesis of indoles via 6pi-electrocyclic ring closures of trienecarbamates."],"pmcid":["PMC2597544"],"funding_grant_id":["R01 GM028663-24","GM28533","R01 GM028663","R01 GM028663-27","R01 GM028663-28","R01 GM028663-25","R01 GM028663-26"],"pubmed_authors":["Greshock TJ","Funk RL"],"additional_accession":[]},"is_claimable":false,"name":"Synthesis of indoles via 6pi-electrocyclic ring closures of trienecarbamates.","description":"A new method for the preparation of indoles from readily available alpha-haloenones and alpha-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6pi-electrocyclic ring closure and subsequent oxidation to afford protected aniline 4. Upon deprotection and reductive amination, acid 5 underwent clean cyclization to N-acetylindole 6 (Ac2O, NEt3, 130 degrees C). This method has been used to construct a variety of substituted indoles that are not easily prepared by conventional indole annelation methods.","dates":{"release":"2006-01-01T00:00:00Z","publication":"2006 Apr","modification":"2025-04-05T15:11:20.837Z","creation":"2019-03-27T00:19:43Z"},"accession":"S-EPMC2597544","cross_references":{"pubmed":["16608316"],"doi":["10.1021/ja060282o"]}}