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Total synthesis of the carbon18-diterpenoid alkaloids neofinaconitine and 9-deoxylappaconitine

Posted on:2012-11-20Degree:Ph.DType:Thesis
University:Weill Medical College of Cornell UniversityCandidate:Shi, YuanFull Text:PDF
GTID:2461390011965116Subject:Chemistry
Abstract/Summary:
The C18- and C19-diterpenoid alkaloids are a family of natural products called norditerpenoids collectively. They are isolated from the plant genera Aconitum and Delphinium, and exhibit pronounced pharmarcological activities including analgesia, antiarrhythmia and anti-inflammation. Their intriguing biological activities and complicated polycyclic core structures prompted us to pursue the synthesis of these natural products.;A convergent synthetic strategy was developed, highlighting a diastereoselective Diels-Alder cycloaddition to assemble all of the carbon atoms required for norditerpenoid alkaloids. An N-acyliminium cyclization and a radical cyclization were enlisted to forge the complete carbocyclic core skeleton. Our approach was successfully applied to the total synthesis of neofinaconitine and 9-deoxylappaconitine.
Keywords/Search Tags:Synthesis, Alkaloids
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