CER - Central Repository
Institute of Chemistry, Technology and Metallurgy
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrillic)
    • Serbian (Latin)
  • Login
View Item 
  •   CER
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
  •   CER
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations

Authorized Users Only
2013
Authors
Tasić, Gordana
Ranđelović, Jelena
Vusurović, Nikola
Maslak, Veselin
Husinec, Suren
Savić, Vladimir
Article (Published version)
Metadata
Show full item record
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.
Keywords:
Bicyclic compounds / Heck reaction / Regioselectivity / Corialstonine / Corialstonidine
Source:
Tetrahedron Letters, 2013, 54, 18, 2243-2246
Publisher:
  • Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
  • Computational design, synthesis and biological evaluation of new heterocyclic compounds as selective tumorogenesis inhibitors (RS-172009)
  • High-Performance Computing Infrastructure for South East Europe's Research Communities (EU-261499)

DOI: 10.1016/j.tetlet.2013.02.068

ISSN: 0040-4039

WoS: 000317640800009

Scopus: 2-s2.0-84875719109
[ Google Scholar ]
4
4
URI
http://cherry.chem.bg.ac.rs/handle/123456789/1586
http://farfar.pharmacy.bg.ac.rs/handle/123456789/1924
https://cer.ihtm.bg.ac.rs/handle/123456789/3504
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
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  - https://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  - Oxford : Pergamon-Elsevier Science Ltd
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",
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 = "Oxford : Pergamon-Elsevier Science Ltd",
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. in Tetrahedron Letters
Oxford : Pergamon-Elsevier Science Ltd., 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 Letters. 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 Letters, 54, no. 18 (2013):2243-2246,
https://doi.org/10.1016/j.tetlet.2013.02.068 . .

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

re3dataOpenAIRERCUB
 

 

All of DSpaceInstitutions/communitiesAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

re3dataOpenAIRERCUB