{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Trost BM"],"funding":["NIGMS NIH HHS"],"pagination":["6054-5"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC2585983"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["128(18)"],"pubmed_abstract":["New classes of nucleophiles, pyrroles, and N-methoxyamides were developed for Pd-catalyzed AAA reactions. By varying the functional groups at the 2-position of pyrroles, either regioisomer of the piperazinone is available. Using one regioisomer, the total synthesis of (+)-agelastatin A in 10 total steps is accomplished. For this synthesis, a new copper-catalyzed aziridination and an indium-catalyzed oxidative ring opening of a N-tosylaziridine were developed. The feasibility of accessing (-)-agelastatin A from the same enantiomer of the chiral catalyst from the other regioisomeric piperazinone is indicated."],"journal":["Journal of the American Chemical Society"],"pubmed_title":["New class of nucleophiles for palladium-catalyzed asymmetric allylic alkylation. Total synthesis of agelastatin A."],"pmcid":["PMC2585983"],"funding_grant_id":["R01 GM013598-42","GM13598","R01 GM013598"],"pubmed_authors":["Dong G","Trost BM"],"additional_accession":[]},"is_claimable":false,"name":"New class of nucleophiles for palladium-catalyzed asymmetric allylic alkylation. Total synthesis of agelastatin A.","description":"New classes of nucleophiles, pyrroles, and N-methoxyamides were developed for Pd-catalyzed AAA reactions. By varying the functional groups at the 2-position of pyrroles, either regioisomer of the piperazinone is available. Using one regioisomer, the total synthesis of (+)-agelastatin A in 10 total steps is accomplished. For this synthesis, a new copper-catalyzed aziridination and an indium-catalyzed oxidative ring opening of a N-tosylaziridine were developed. The feasibility of accessing (-)-agelastatin A from the same enantiomer of the chiral catalyst from the other regioisomeric piperazinone is indicated.","dates":{"release":"2006-01-01T00:00:00Z","publication":"2006 May","modification":"2025-04-05T11:51:59.712Z","creation":"2019-03-26T23:28:29Z"},"accession":"S-EPMC2585983","cross_references":{"pubmed":["16669672"],"doi":["10.1021/ja061105q"]}}