A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations
Authorized Users Only
2013
Authors
Tasić, GordanaRanđelović, Jelena
Vusurović, Nikola
Maslak, Veselin

Husinec, Suren
Savić, Vladimir

Article (Published version)

Metadata
Show full item recordAbstract
Intramolecular Pd-catalysed cyclisation reactions for the preparation of bicyclic compounds have been studied as a model system towards the synthesis of corialstonine and corialstonidine. Significant differences in reactivity have been observed for the cyclic allyl alcohols possessing O-protected and free OH functionalities. Cyclisation via the intramolecular Heck reaction, for both derivatives, proved to be highly regioselective and while the O-protected compound favoured the exo mode of cyclisation, the unprotected alcohol preferred the endo cyclisation pathway. Brief computational studies were carried out in order to obtain further insight into these processes.
Keywords:
Bicyclic compounds / Heck reaction / Regioselectivity / Corialstonine / CorialstonidineSource:
Tetrahedron Letters, 2013, 54, 18, 2243-2246Publisher:
- Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
- Computational design, synthesis and biological evaluation of new heterocyclic compounds as selective tumorogenesis inhibitors (RS-172009)
- High-Performance Computing Infrastructure for South East Europe's Research Communities (EU-261499)
DOI: 10.1016/j.tetlet.2013.02.068
ISSN: 0040-4039
WoS: 000317640800009
Scopus: 2-s2.0-84875719109
URI
http://cherry.chem.bg.ac.rs/handle/123456789/1586http://farfar.pharmacy.bg.ac.rs/handle/123456789/1924
https://cer.ihtm.bg.ac.rs/handle/123456789/3504
Collections
Institution/Community
IHTMTY - JOUR AU - Tasić, Gordana AU - Ranđelović, Jelena AU - Vusurović, Nikola AU - Maslak, Veselin AU - Husinec, Suren AU - Savić, Vladimir PY - 2013 UR - http://cherry.chem.bg.ac.rs/handle/123456789/1586 UR - http://farfar.pharmacy.bg.ac.rs/handle/123456789/1924 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3504 AB - Intramolecular Pd-catalysed cyclisation reactions for the preparation of bicyclic compounds have been studied as a model system towards the synthesis of corialstonine and corialstonidine. Significant differences in reactivity have been observed for the cyclic allyl alcohols possessing O-protected and free OH functionalities. Cyclisation via the intramolecular Heck reaction, for both derivatives, proved to be highly regioselective and while the O-protected compound favoured the exo mode of cyclisation, the unprotected alcohol preferred the endo cyclisation pathway. Brief computational studies were carried out in order to obtain further insight into these processes. PB - Oxford : Pergamon-Elsevier Science Ltd T2 - Tetrahedron Letters T1 - A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations VL - 54 IS - 18 SP - 2243 EP - 2246 DO - 10.1016/j.tetlet.2013.02.068 ER -
@article{ author = "Tasić, Gordana and Ranđelović, Jelena and Vusurović, Nikola and Maslak, Veselin and Husinec, Suren and Savić, Vladimir", year = "2013", abstract = "Intramolecular Pd-catalysed cyclisation reactions for the preparation of bicyclic compounds have been studied as a model system towards the synthesis of corialstonine and corialstonidine. Significant differences in reactivity have been observed for the cyclic allyl alcohols possessing O-protected and free OH functionalities. Cyclisation via the intramolecular Heck reaction, for both derivatives, proved to be highly regioselective and while the O-protected compound favoured the exo mode of cyclisation, the unprotected alcohol preferred the endo cyclisation pathway. Brief computational studies were carried out in order to obtain further insight into these processes.", publisher = "Oxford : Pergamon-Elsevier Science Ltd", journal = "Tetrahedron Letters", title = "A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations", volume = "54", number = "18", pages = "2243-2246", doi = "10.1016/j.tetlet.2013.02.068" }
Tasić, G., Ranđelović, J., Vusurović, N., Maslak, V., Husinec, S.,& Savić, V.. (2013). A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations. in Tetrahedron Letters Oxford : Pergamon-Elsevier Science Ltd., 54(18), 2243-2246. https://doi.org/10.1016/j.tetlet.2013.02.068
Tasić G, Ranđelović J, Vusurović N, Maslak V, Husinec S, Savić V. A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations. in Tetrahedron Letters. 2013;54(18):2243-2246. doi:10.1016/j.tetlet.2013.02.068 .
Tasić, Gordana, Ranđelović, Jelena, Vusurović, Nikola, Maslak, Veselin, Husinec, Suren, Savić, Vladimir, "A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations" in Tetrahedron Letters, 54, no. 18 (2013):2243-2246, https://doi.org/10.1016/j.tetlet.2013.02.068 . .