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

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2013
Authors
Tasić, Gordana
Ranđelović, Jelena
Vusurović, Nikola
Maslak, Veselin
Husinec, Suren
Savić, Vladimir
Article (Published version)
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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-Asymmetry, 2013, 54, 18, 2243-2246
Publisher:
  • Pergamon-Elsevier Science Ltd, Oxford
Projects:
  • Computational design, synthesis and biological evaluation of new heterocyclic compounds as selective tumorogenesis inhibitors (RS-172009)

DOI: 10.1016/j.tetlet.2013.02.068

ISSN: 0040-4039

WoS: 000317640800009

Scopus: 2-s2.0-84875719109
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URI
http://farfar.pharmacy.bg.ac.rs/handle/123456789/1924
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  • Radovi istraživača / Researchers’ publications
Institution
Pharmacy

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