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 recordAbstract
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 / CorialstonidineSource:
Tetrahedron-Asymmetry, 2013, 54, 18, 2243-2246Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Projects:
DOI: 10.1016/j.tetlet.2013.02.068
ISSN: 0040-4039