{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Gu H"],"funding":["Natural Science Foundation of Hebei Province","Research Grants Council, University Grants Committee","Hebei Provincial Department of Human Resources and Social Security","Hebei Normal University"],"pagination":["2164-2168"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC12671562"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["17(4)"],"pubmed_abstract":["Aogacillins A and B, circumventors of arbekacin resistance in MRSA, possess a densely oxidized spirolactone moiety and an electron deficient terminal exocyclic double bond. This represents a challenging target for total synthesis. Herein, the evolution of a successful strategy for the total synthesis of <i>ent</i>-aogacillin A and aogacillin B is described. Although the spirocyclic skeleton could be efficiently constructed by the Achmatowicz rearrangement-based strategy, the elaboration of the dihydropyranone moiety to the fully functionalized lactone of aogacillins was not successful. A new strategy is proposed and successfully implemented, which features allylic C-H oxidation and a one-pot sequential aldol reaction and lactonization. This enables us to achieve the first and asymmetric to"],"journal":["Chemical science"],"pubmed_title":["Total syntheses of <i>ent</i>-aogacillin A and aogacillin B."],"pmcid":["PMC12671562"],"funding_grant_id":["16304023","C20230340","B2023205007","16303524","16308922","C6022-22W","L2023B17"],"pubmed_authors":["Tong R","Zhang W","Li X","Ma B","Qiu W","Yang Z","Li Z","Gu H","Sang R","Ren J","Zhang X","Chen X"],"additional_accession":[]},"is_claimable":false,"name":"Total syntheses of <i>ent</i>-aogacillin A and aogacillin B.","description":"Aogacillins A and B, circumventors of arbekacin resistance in MRSA, possess a densely oxidized spirolactone moiety and an electron deficient terminal exocyclic double bond. This represents a challenging target for total synthesis. Herein, the evolution of a successful strategy for the total synthesis of <i>ent</i>-aogacillin A and aogacillin B is described. Although the spirocyclic skeleton could be efficiently constructed by the Achmatowicz rearrangement-based strategy, the elaboration of the dihydropyranone moiety to the fully functionalized lactone of aogacillins was not successful. A new strategy is proposed and successfully implemented, which features allylic C-H oxidation and a one-pot sequential aldol reaction and lactonization. This enables us to achieve the first and asymmetric to","dates":{"release":"2026-01-01T00:00:00Z","publication":"2026 Jan","modification":"2026-06-17T04:53:42.521Z","creation":"2026-06-17T03:06:19.587Z"},"accession":"S-EPMC12671562","cross_references":{"pubmed":["41340921"],"doi":["10.1039/d5sc04554a"]}}