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

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. (C) 2015 Elsevier Ltd. All rights reserved.