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.
TY - 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 - http://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 - Pergamon-Elsevier Science Ltd, Oxford
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",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1586, http://farfar.pharmacy.bg.ac.rs/handle/123456789/1924, http://cer.ihtm.bg.ac.rs/handle/123456789/3504",
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 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.
Tetrahedron Letters
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. Tetrahedron Letters. 2013;54(18):2243-2246
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" Tetrahedron Letters, 54, no. 18 (2013):2243-2246,
https://doi.org/10.1016/j.tetlet.2013.02.068 .
