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Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone
dc.creator | Trajković, Milos | |
dc.creator | Ferjančić, Zorana | |
dc.creator | Saičić, Radomir | |
dc.creator | Bihelović, Filip | |
dc.date.accessioned | 2019-04-09T11:15:47Z | |
dc.date.available | 2020-02-04 | |
dc.date.available | 2020-02-04 | |
dc.date.issued | 2019 | |
dc.identifier.issn | 0947-6539 | |
dc.identifier.uri | https://cherry.chem.bg.ac.rs/handle/123456789/2874 | |
dc.description.abstract | A chiral-pool-based synthesis of the platensimycin core was achieved using (S)-lactic acid as an inexpensive starting material. The cyclohexenone ring was closed in a Mukaiyama–Michael domino sequence, while the quaternary stereocenter was created by a highly stereoselective decarboxylative allylation. The spirobicyclic skeleton was constructed by a RCM reaction. A new silver(I)-promoted cyclization reaction of Δ 6 - and Δ 7 -α-iodoketones was developed and applied for the pivotal carbon–carbon bond formation. The scope and limitations of this methodology are also presented. | |
dc.publisher | Wiley | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172027/RS// | |
dc.relation | info:eu-repo/grantAgreement/EC/FP7/256716/EU// | |
dc.rights | embargoedAccess | |
dc.source | Chemistry - A European Journal | |
dc.subject | antibiotics | |
dc.subject | cyclization | |
dc.subject | natural products | |
dc.subject | silver | |
dc.subject | total synthesis | |
dc.title | Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone | |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Трајковић, Милос; Бихеловић, Филип; Ферјанчић, Зорана; Саичић, Радомир Н.; | |
dc.citation.volume | 25 | |
dc.citation.issue | 17 | |
dc.citation.spage | 4340 | |
dc.citation.epage | 4344 | |
dc.identifier.wos | 000462057300014 | |
dc.identifier.doi | 10.1002/chem.201900497 | |
dc.citation.rank | M21~ | |
dc.description.other | This is the peer-reviewed version of the following article:Trajković, M.; Ferjančić, Z.; Saičić, R. N.; Bihelović, F. Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone. Chemistry - A European Journal 2019, 25 (17), 4340–4344. [https://doi.org/10.1002/chem.201900497]. | |
dc.description.other | Supplementary material: [http://cherry.chem.bg.ac.rs/handle/123456789/3842] | |
dc.type.version | acceptedVersion | |
dc.identifier.scopus | 2-s2.0-85062044339 | |
dc.identifier.fulltext | https://cherry.chem.bg.ac.rs/bitstream/id/6652/10.1002@chem.201900497.pdf |