The intramolecular Heck reaction has been examined for the preparation of the core bicyclic structure of corialstonidine. Initial attempts to cyclise a vinyl iodide moiety onto a cyclic allyl alcohol were complicated by various side reactions. However, the corresponding process performed under reductive conditions on a conjugated ketone, obtained from the cyclic allyl alcohol, afforded the desired bicyclo[3.2.1] derivative. This compound possesses the skeletal features of the carbocyclic fragment of corialstonidine and is suitable for further transformations aimed towards the synthesis of the natural product or its derivatives.
TY - JOUR
AU - Tasić, Gordana
AU - Maslak, Veselin
AU - Husinec, Suren
AU - Todorović, Nina
AU - Savić, Vladimir
PY - 2015
UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2375
AB - The intramolecular Heck reaction has been examined for the preparation of the core bicyclic structure of corialstonidine. Initial attempts to cyclise a vinyl iodide moiety onto a cyclic allyl alcohol were complicated by various side reactions. However, the corresponding process performed under reductive conditions on a conjugated ketone, obtained from the cyclic allyl alcohol, afforded the desired bicyclo[3.2.1] derivative. This compound possesses the skeletal features of the carbocyclic fragment of corialstonidine and is suitable for further transformations aimed towards the synthesis of the natural product or its derivatives.
PB - Pergamon-Elsevier Science Ltd, Oxford
T2 - Tetrahedron-Asymmetry
T1 - Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine
VL - 56
IS - 19
SP - 2529
EP - 2532
DO - 10.1016/j.tetlet.2015.03.129
ER -
@article{
author = "Tasić, Gordana and Maslak, Veselin and Husinec, Suren and Todorović, Nina and Savić, Vladimir",
year = "2015",
abstract = "The intramolecular Heck reaction has been examined for the preparation of the core bicyclic structure of corialstonidine. Initial attempts to cyclise a vinyl iodide moiety onto a cyclic allyl alcohol were complicated by various side reactions. However, the corresponding process performed under reductive conditions on a conjugated ketone, obtained from the cyclic allyl alcohol, afforded the desired bicyclo[3.2.1] derivative. This compound possesses the skeletal features of the carbocyclic fragment of corialstonidine and is suitable for further transformations aimed towards the synthesis of the natural product or its derivatives.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron-Asymmetry",
title = "Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine",
volume = "56",
number = "19",
pages = "2529-2532",
doi = "10.1016/j.tetlet.2015.03.129"
}
Tasić, G., Maslak, V., Husinec, S., Todorović, N.,& Savić, V.. (2015). Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine. in Tetrahedron-Asymmetry
Pergamon-Elsevier Science Ltd, Oxford., 56(19), 2529-2532.
https://doi.org/10.1016/j.tetlet.2015.03.129
Tasić G, Maslak V, Husinec S, Todorović N, Savić V. Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine. in Tetrahedron-Asymmetry. 2015;56(19):2529-2532.
doi:10.1016/j.tetlet.2015.03.129 .
Tasić, Gordana, Maslak, Veselin, Husinec, Suren, Todorović, Nina, Savić, Vladimir, "Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine" in Tetrahedron-Asymmetry, 56, no. 19 (2015):2529-2532,
https://doi.org/10.1016/j.tetlet.2015.03.129 . .
