{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Ghosh AK"],"funding":["Purdue University","National Institute of General Medical Sciences","NIGMS NIH HHS"],"pagination":["5187-5198"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC5972027"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["83(9)"],"pubmed_abstract":["Thailanstatin A has been isolated recently from the fermentation broth of B. thailandensis MSMB43. We describe here an enantioselective convergent synthesis of thailanstatin A methyl ester and evaluation of its splicing activity. Synthesis of both highly functionalized tetrahydropyran rings were carried out from commercially available tri- O-acetyl-d-glucal as the key starting material. Our convergent synthesis involved the synthesis of both tetrahydropyran fragments in a highly stereoselective manner. The fragments were then coupled using cross-metathesis as the key step. The synthesis of the diene subunit included a highly stereoselective Claisen rearrangement, a Cu(I)-mediated conjugate addition of MeLi to set the C-14 methyl stereochemistry, a reductive amination reaction to install th"],"journal":["The Journal of organic chemistry"],"pubmed_title":["Enantioselective Synthesis of Thailanstatin A Methyl Ester and Evaluation of in Vitro Splicing Inhibition."],"pmcid":["PMC5972027"],"funding_grant_id":["GM122279","T32 GM008646","R37 GM053386","R01 GM122279"],"pubmed_authors":["Nie S","MacRae AJ","Jurica MS","Veitschegger AM","Ghosh AK","Relitti N"],"additional_accession":[]},"is_claimable":false,"name":"Enantioselective Synthesis of Thailanstatin A Methyl Ester and Evaluation of in Vitro Splicing Inhibition.","description":"Thailanstatin A has been isolated recently from the fermentation broth of B. thailandensis MSMB43. We describe here an enantioselective convergent synthesis of thailanstatin A methyl ester and evaluation of its splicing activity. Synthesis of both highly functionalized tetrahydropyran rings were carried out from commercially available tri- O-acetyl-d-glucal as the key starting material. Our convergent synthesis involved the synthesis of both tetrahydropyran fragments in a highly stereoselective manner. The fragments were then coupled using cross-metathesis as the key step. The synthesis of the diene subunit included a highly stereoselective Claisen rearrangement, a Cu(I)-mediated conjugate addition of MeLi to set the C-14 methyl stereochemistry, a reductive amination reaction to install th","dates":{"release":"2018-01-01T00:00:00Z","publication":"2018 May","modification":"2025-04-22T01:37:35.14Z","creation":"2019-06-06T23:03:51Z"},"accession":"S-EPMC5972027","cross_references":{"pubmed":["29696980"],"doi":["10.1021/acs.joc.8b00593"]}}