Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine
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.
Keywords:
Heck reaction / Corialstonidine / Bicyclic ketoneSource:
Tetrahedron-Asymmetry, 2015, 56, 19, 2529-2532Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
DOI: 10.1016/j.tetlet.2015.03.129
ISSN: 0040-4039
WoS: 000353751000035
Scopus: 2-s2.0-84937762963
Collections
Institution/Community
PharmacyTY - 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 . .