{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Winkler JD"],"funding":["NCI NIH HHS"],"pagination":["9726-8"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC3398804"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["124(33)"],"pubmed_abstract":["The first total synthesis of (+/-)-ingenol has been achieved. The key features of the synthesis include the use of a highly diastereoselective Michael reaction to fix the C-11 methyl stereochemistry and the incorporation of the dimethylcyclopropane via diastereoselective carbene addition to the Delta13,14 olefin. The intramolecular dioxenone photoaddition-fragmentation sequence leads to the establishment of the critical C-8/C-10 trans intrabridgehead stereochemistry, a central challenge in the synthesis of ingenanes. The completion of the synthesis proceeds using the C-6alpha hydroxymethyl group as the sole handle for oxidation of seven contiguous carbon centers."],"journal":["Journal of the American Chemical Society"],"pubmed_title":["The first total synthesis of (+/-)-ingenol."],"pmcid":["PMC3398804"],"funding_grant_id":["CA45686","R01 CA040250","CA40250"],"pubmed_authors":["Winkler JD","Jeon YT","Rouse MB","Greaney MF","Harrison SJ"],"additional_accession":[]},"is_claimable":false,"name":"The first total synthesis of (+/-)-ingenol.","description":"The first total synthesis of (+/-)-ingenol has been achieved. The key features of the synthesis include the use of a highly diastereoselective Michael reaction to fix the C-11 methyl stereochemistry and the incorporation of the dimethylcyclopropane via diastereoselective carbene addition to the Delta13,14 olefin. The intramolecular dioxenone photoaddition-fragmentation sequence leads to the establishment of the critical C-8/C-10 trans intrabridgehead stereochemistry, a central challenge in the synthesis of ingenanes. The completion of the synthesis proceeds using the C-6alpha hydroxymethyl group as the sole handle for oxidation of seven contiguous carbon centers.","dates":{"release":"2002-01-01T00:00:00Z","publication":"2002 Aug","modification":"2025-04-18T16:16:07.167Z","creation":"2019-03-27T00:55:42Z"},"accession":"S-EPMC3398804","cross_references":{"pubmed":["12175229"],"doi":["10.1021/ja026600a"]}}