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. (C) 2015 Elsevier Ltd. All rights reserved.
Keywords:
Heck reaction / Corialstonidine / Bicyclic ketoneSource:
Tetrahedron Letters, 2015, 56, 19, 2529-2532Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
- Computational design, synthesis and biological evaluation of new heterocyclic compounds as selective tumorogenesis inhibitors (RS-MESTD-Basic Research (BR or ON)-172009)
Note:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3432
DOI: 10.1016/j.tetlet.2015.03.129
ISSN: 0040-4039
WoS: 000353751000035
Scopus: 2-s2.0-84937762963
Collections
Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Tasić, Gordana AU - Maslak, Veselin AU - Husinec, Suren AU - Todorović, Nina AU - Savić, Vladimir PY - 2015 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1700 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. (C) 2015 Elsevier Ltd. All rights reserved. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Tetrahedron Letters 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. (C) 2015 Elsevier Ltd. All rights reserved.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Tetrahedron Letters", 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 Letters 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 Letters. 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 Letters, 56, no. 19 (2015):2529-2532, https://doi.org/10.1016/j.tetlet.2015.03.129 . .