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A study towards the synthesis of (-)-atrop-abyssomicin C core
dc.creator | Saičić, Radomir | |
dc.creator | Trmčić, Milena | |
dc.date.accessioned | 2022-05-10T09:14:03Z | |
dc.date.available | 2022-05-10T09:14:03Z | |
dc.date.issued | 2021 | |
dc.identifier.issn | 0352-5139 | |
dc.identifier.uri | http://www.doiserbia.nb.rs/Article.aspx?id=0352-51392100099S | |
dc.identifier.uri | http://cherry.chem.bg.ac.rs/handle/123456789/5044 | |
dc.description.abstract | An attempt to synthesize the cyclohexane core of antibiotic abyssomicin C is described. The initial, protecting group-free approach (relying on internal protection) failed and had to be modified, in order to allow for efficient deprotection of the acid-sensitive cyclization precursor in the penultimate synthetic step. Thus, a pyranoside structural unit was used as a latent lactone/ester functionality, which was deprotected via thioacetalization/hydrolysis/oxidation sequence, to give the δ-valerolactone-type cyclization precursor. Unfortunately, the key cyclization reaction was not feasible, even after structural modification of the cyclization precursor. Reluctance towards cyclization turned out to be a general property of (at least some) Δ7-unsaturated esters, which required the development of a new strategy for this type of transformation. | |
dc.language | en | |
dc.publisher | Belgrade : Serbian Chemical Society | |
dc.rights | openAccess | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.source | Journal of the Serbian Chemical Society | |
dc.source | Journal of the Serbian Chemical Society | |
dc.subject | organic synthesis | |
dc.subject | cyclization | |
dc.subject | protecting groups | |
dc.subject | pyranoside. | |
dc.subject | natural products | |
dc.title | A study towards the synthesis of (-)-atrop-abyssomicin C core | |
dc.type | article | en |
dc.type | article | |
dc.rights.license | BY-NC-ND | |
dc.citation.volume | 86 | |
dc.citation.issue | 12 | |
dc.citation.spage | 1305 | |
dc.citation.epage | 1315 | |
dc.identifier.wos | 000744174800014 | |
dc.identifier.doi | 10.2298/JSC211001099S | |
dc.citation.rank | M23 | |
dc.type.version | publishedVersion | |
dc.identifier.scopus | 2-s2.0-85124622589 | |
dc.identifier.fulltext | http://cherry.chem.bg.ac.rs/bitstream/id/29572/bitstream_29572.pdf |