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Title: Palladium-catalysed [2+3] cycloaddition routes to the tricyclic core of the stenine group of Stemona alkaloids
Author: Neary, Vincent John
ISNI:       0000 0001 3440 4570
Awarding Body: Loughborough University
Current Institution: Loughborough University
Date of Award: 2007
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The stemona alkaloids have generated considerable interest in recent years. They are from the Stemonaceae family, which has two genera, Stemona and Croomia and are a structurally interesting class of alkaloids isolated from the roots and rhizomes of the Stemonaceae plant family. Common to all of the Stemona alkaloids is the central azapinoindole, (B, C, D system) shown in stenine below. The route to the stenine core which we wished to look at, envisaged using a Pd(0) catalysed [2+3] cycloaddition between an activated vinylcyclopropane substrate and a suitable imine to give the hydro indole core. A subsequent intramolecular Heck reaction could then be carried out to construct the seven-membered azepine ring of the tricylic core. We have already established Pd(0) catalysed [2+3] cycloaddition routes to five-membered heterocylces via the trapping of various imines with vinylcyclopropanes and we hope that using this methodology we can access the tricyclic core of stenine.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Chemical Sciences not elsewhere classified