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Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine

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2015
Authors
Tasić, Gordana
Maslak, Veselin
Husinec, Suren
Todorović, Nina
Savić, Vladimir
Article (Published version)
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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 ketone
Source:
Tetrahedron-Asymmetry, 2015, 56, 19, 2529-2532
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.2015.03.129

ISSN: 0040-4039

WoS: 000353751000035

Scopus: 2-s2.0-84937762963
[ Google Scholar ]
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URI
http://farfar.pharmacy.bg.ac.rs/handle/123456789/2375
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  • Radovi istraživača / Researchers’ publications
Institution
Pharmacy

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