{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Guarneros-Cruz KA"],"funding":["Consejo Nacional de Humanidades, Ciencias y Tecnolog?as","Vicerrector?a de Investigaci?n y Estudios de Posgrado, Benem?rita Universidad Aut?noma de Puebla"],"pagination":["15808-15821"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC11536364"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["89(21)"],"pubmed_abstract":["Despite the enormous importance of chromone and flavonoid piperidine alkaloids, a general method for their synthesis has not been described. Accordingly, from simple tetrahydro-3-pyridinemethanols (<b>A</b>) and phenol derivatives (<b>B</b>), a synthetic approach to chromone and flavonoid piperidine alkaloids is presented. The access to a novel chromone and flavonoid alkaloid precursors 4-(2-hydroxyphenyl)-3-methylenepiperidines (<b>C</b>) is achieved in only two steps: Mitsunobu reaction followed by an intramolecular C-H phenolization via an aromatic Claisen rearrangement of the respective Mitsunobu adducts (<b>D</b>). Consequently, the simultaneous installation of the functionalized phenol group and the exo-methylene group within the piperidine skeleton, permits, not only the easy construction of the chromone or flavonoid cores but also the simultaneous installation of the hydroxyl group with the required <i>cis</i>-orientation. Additionally, the synthetic utility of this novel approach is showcased in the formal synthesis of flavopiridol, rohitukine, and their <i>N</i>-Moc analogues."],"journal":["The Journal of organic chemistry"],"pubmed_title":["Synthetic Approach to Chromone and Flavonoid Piperidine Alkaloids."],"pmcid":["PMC11536364"],"funding_grant_id":["00321-PV/2024","A1-S-18230"],"pubmed_authors":["Cruz-Gregorio S","Guarneros-Cruz KA","Romero-Ibanez J","Meza-Leon RL","Sartillo-Piscil F"],"additional_accession":[]},"is_claimable":false,"name":"Synthetic Approach to Chromone and Flavonoid Piperidine Alkaloids.","description":"Despite the enormous importance of chromone and flavonoid piperidine alkaloids, a general method for their synthesis has not been described. Accordingly, from simple tetrahydro-3-pyridinemethanols (<b>A</b>) and phenol derivatives (<b>B</b>), a synthetic approach to chromone and flavonoid piperidine alkaloids is presented. The access to a novel chromone and flavonoid alkaloid precursors 4-(2-hydroxyphenyl)-3-methylenepiperidines (<b>C</b>) is achieved in only two steps: Mitsunobu reaction followed by an intramolecular C-H phenolization via an aromatic Claisen rearrangement of the respective Mitsunobu adducts (<b>D</b>). Consequently, the simultaneous installation of the functionalized phenol group and the exo-methylene group within the piperidine skeleton, permits, not only the easy construction of the chromone or flavonoid cores but also the simultaneous installation of the hydroxyl group with the required <i>cis</i>-orientation. Additionally, the synthetic utility of this novel approach is showcased in the formal synthesis of flavopiridol, rohitukine, and their <i>N</i>-Moc analogues.","dates":{"release":"2024-01-01T00:00:00Z","publication":"2024 Nov","modification":"2025-04-20T03:55:09.971Z","creation":"2025-04-20T03:55:09.971Z"},"accession":"S-EPMC11536364","cross_references":{"pubmed":["39437173"],"doi":["10.1021/acs.joc.4c01926"]}}