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dc.contributor.authorTimothy J. Donohoe Prof.
dc.contributor.authorHerman O. Sintim Dr.
dc.contributor.authorLeena Sisangia Dr.
dc.contributor.authorKarl W. Ace Dr.
dc.contributor.authorPaul M. Guyo Dr.
dc.contributor.authorAndrew Cowley Dr.
dc.contributor.authorJohn D. Harling Dr
dc.date.accessioned2012-10-23T09:19:45Z
dc.date.available2012-10-23T09:19:45Z
dc.date.issued2005-05-02
dc.identifier.citationDOI: 10.1002/chem.200401119en_US
dc.identifier.urihttp://hdl.handle.net/123456789/328
dc.descriptionthe original publication is available at http://onlinelibrary.wiley.com/doi/10.1002/chem.200401119/fullen_US
dc.description.abstractA new synthesis of the 20S proteasome inhibitor clasto-lactacystin β-lactone is described. Our route to this important natural product involves the partial reduction of an electron deficient pyrrole as a key step. By judicious choice of enolate counterion, we were able to exert complete control over the stereoselectivity of the reduction/aldol reaction. Early attempts to complete the synthesis by using a C-4 methyl substituted pyrrole are described in full, together with our attempts to promote regioselective elimination of a tertiary alcohol. The lessons learnt from this first approach led us to develop another, and ultimately successful, route that introduced the C-4 methyl group at a late stage in the synthesis. Our successful route is then described and this contains several highly stereoselective steps including a cis-dihydroxylation and an enolate methylation. The final synthesis proceeds in just 13 steps and in 15 % overall yield making it an extremely efficient route to this valuable compound.en_US
dc.description.sponsorshipPwani Universityen_US
dc.language.isoenen_US
dc.publisherWiley Online Libraryen_US
dc.subjectlactacystinen_US
dc.subjectnatural productsen_US
dc.subjectpyrrolesen_US
dc.titleUtility of the Ammonia-Free Birch Reduction of Electron-Deficient Pyrroles: Total Synthesis of the 20S Proteasome Inhibitor, clasto-Lactacystin β-Lactoneen_US
dc.typeArticleen_US


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