{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Hafeman NJ"],"funding":["Division of Chemistry","Heritage Medical Research Institute","National Institute of General Medical Sciences","NIGMS NIH HHS"],"pagination":["20232-20236"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC9997676"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["144(44)"],"pubmed_abstract":["The first total synthesis of the furanobutenolide-derived cembranoid diterpenoid havellockate is disclosed. Our convergent strategy employs a Julia-Kocienski olefination to join two enantioenriched fragments to produce a diene that is subsequently used in a propiolic acid esterification/Diels-Alder cascade. This sequence generates the fused carbocyclic core of the natural product in short order. A challenging Zn-mediated Barbier allylation then forges the final C-C bond and also establishes two vicinal stereogenic centers. Finally, a Cu-catalyzed aerobic oxidation facilitates the formation of the β-hydroxybutanolide to complete the total synthesis."],"journal":["Journal of the American Chemical Society"],"pubmed_title":["Asymmetric Total Synthesis of Havellockate."],"pmcid":["PMC9997676"],"funding_grant_id":["R35GM145239","R35 GM145239","CHE1800511","R01 GM080269"],"pubmed_authors":["Fulton TJ","Alexy EJ","Chan M","Stoltz BM","Hafeman NJ","Loskot SA","Virgil SC"],"additional_accession":[]},"is_claimable":false,"name":"Asymmetric Total Synthesis of Havellockate.","description":"The first total synthesis of the furanobutenolide-derived cembranoid diterpenoid havellockate is disclosed. Our convergent strategy employs a Julia-Kocienski olefination to join two enantioenriched fragments to produce a diene that is subsequently used in a propiolic acid esterification/Diels-Alder cascade. This sequence generates the fused carbocyclic core of the natural product in short order. A challenging Zn-mediated Barbier allylation then forges the final C-C bond and also establishes two vicinal stereogenic centers. Finally, a Cu-catalyzed aerobic oxidation facilitates the formation of the β-hydroxybutanolide to complete the total synthesis.","dates":{"release":"2022-01-01T00:00:00Z","publication":"2022 Nov","modification":"2025-04-04T21:13:35.356Z","creation":"2025-04-04T21:13:35.356Z"},"accession":"S-EPMC9997676","cross_references":{"pubmed":["36287147"],"doi":["10.1021/jacs.2c09583"]}}