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Synfacts 2007(9): 0895-0895
DOI: 10.1055/s-2007-968841
DOI: 10.1055/s-2007-968841
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Baconipyrone C
Contributor(s):Philip KocienskiD. G. Gillingham, A. H. Hoveyda*
Boston College, Chestnut Hill, USA
Chiral N-Heterocyclic Carbenes in Natural Product Synthesis: Application of Ru-Catalyzed Asymmetric Ring-Opening/Cross-Metathesis and Cu-Catalyzed Allylic Alkylation to Total Synthesis of Baconipyrone C
Angew. Chem. Int. Ed. 2007, 46: 3860-3864
Boston College, Chestnut Hill, USA
Chiral N-Heterocyclic Carbenes in Natural Product Synthesis: Application of Ru-Catalyzed Asymmetric Ring-Opening/Cross-Metathesis and Cu-Catalyzed Allylic Alkylation to Total Synthesis of Baconipyrone C
Angew. Chem. Int. Ed. 2007, 46: 3860-3864
Further Information
Publication History
Publication Date:
23 August 2007 (online)
Key words
allylic alkylation - asymmetric ring-closing metathesis - copper - ruthenium - N-heterocyclic carbenes - desymmetrization
Significance
A new chiral Ru-based N-heterocyclic carbene complex F was deployed in the first asymmetric Ru-catalyzed asymmetric olefin metathesis reaction (E to G). New Ag- and Cu-based N-heterocyclic carbene complexes were used in catalytic asymmetric allylic alkylation reactions (e.g. A to C).
Comment
The high er obtained in the conversion of A to C demonstrates that allylic alkylation is under catalyst control whereas in the conversion of J to K, substrate control governs the diastereoselectivity.