Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine
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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
- Pergamon-Elsevier Science Ltd, Oxford