{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["15(32)"],"submitter":["Xie K"],"pubmed_abstract":["The Pictet-Spengler type condensation of tryptamine derivatives and aldehydes or ketones is a classic reaction, and has been previously applied to assemble indole-annulated 5-, 6- and 8-membered heterocyclic rings. In this work, we further expand the synthetic scope of this reaction to the 7-membered azepino[4,5-<i>b</i>]indole skeleton through the direct C-H functionalization of 2-alkyl tryptamines, in which the non-activated methylene group participates in a 7-membered ring formation with aldehydes. By combining this unprecedented ring-forming process with a second C-H olefination at the same carbon, the concise total synthesis of natural products ngouniensines is achieved, demonstrating the synthetic potential of the developed chemistry in simplifying retrosynthetic disconnections."],"journal":["Chemical science"],"pagination":["12732-12738"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC11323328"],"repository":["biostudies-literature"],"pubmed_title":["C-H functionalization of 2-alkyl tryptamines: direct assembly of azepino[4,5-<i>b</i>]indoles and total synthesis of ngouniensines."],"pmcid":["PMC11323328"],"pubmed_authors":["Shen Z","Cheng P","Dong H","Xie K","Yu ZX","Zu L"],"additional_accession":[]},"is_claimable":false,"name":"C-H functionalization of 2-alkyl tryptamines: direct assembly of azepino[4,5-<i>b</i>]indoles and total synthesis of ngouniensines.","description":"The Pictet-Spengler type condensation of tryptamine derivatives and aldehydes or ketones is a classic reaction, and has been previously applied to assemble indole-annulated 5-, 6- and 8-membered heterocyclic rings. In this work, we further expand the synthetic scope of this reaction to the 7-membered azepino[4,5-<i>b</i>]indole skeleton through the direct C-H functionalization of 2-alkyl tryptamines, in which the non-activated methylene group participates in a 7-membered ring formation with aldehydes. By combining this unprecedented ring-forming process with a second C-H olefination at the same carbon, the concise total synthesis of natural products ngouniensines is achieved, demonstrating the synthetic potential of the developed chemistry in simplifying retrosynthetic disconnections.","dates":{"release":"2024-01-01T00:00:00Z","publication":"2024 Aug","modification":"2025-04-19T20:38:43.37Z","creation":"2025-04-19T20:38:43.37Z"},"accession":"S-EPMC11323328","cross_references":{"pubmed":["39148802"],"doi":["10.1039/d4sc02802c"]}}