A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations
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2013
Authors
Tasić, GordanaRanđelović, Jelena
Vusurović, Nikola
Maslak, Veselin
Husinec, Suren
Savić, Vladimir
Article (Published version)
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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-Asymmetry, 2013, 54, 18, 2243-2246Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
DOI: 10.1016/j.tetlet.2013.02.068
ISSN: 0040-4039
WoS: 000317640800009
Scopus: 2-s2.0-84875719109
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PharmacyTY - JOUR AU - Tasić, Gordana AU - Ranđelović, Jelena AU - Vusurović, Nikola AU - Maslak, Veselin AU - Husinec, Suren AU - Savić, Vladimir PY - 2013 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1924 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 - Pergamon-Elsevier Science Ltd, Oxford T2 - Tetrahedron-Asymmetry 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 = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Tetrahedron-Asymmetry", 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-Asymmetry Pergamon-Elsevier Science Ltd, Oxford., 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-Asymmetry. 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-Asymmetry, 54, no. 18 (2013):2243-2246, https://doi.org/10.1016/j.tetlet.2013.02.068 . .