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dc.contributor.authorDonohoe, Timothy J.
dc.contributor.authorSintim, Herman O.
dc.contributor.authorSisangia, Leena
dc.contributor.authorAce, Karl W.
dc.contributor.authorGuyo, Paul M.
dc.contributor.authorCowley, Andrew
dc.contributor.authorHarling, John D.
dc.date.accessioned2013-11-20T09:07:53Z
dc.date.available2013-11-20T09:07:53Z
dc.date.issued2005
dc.identifier.otherDOI: 10.1002/chem.200401119
dc.identifier.urihttp://hdl.handle.net/123456789/601
dc.description.abstractA new synthesis of the 20S proteasome inhibitor clasto-lactacystin b-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 compounden_US
dc.language.isoenen_US
dc.publisherChem. Eur. J.en_US
dc.subjectlactacystinen_US
dc.subjectnatural to this valuable compound. productsen_US
dc.subjectpyrrolesen_US
dc.subjecttotal synthesisen_US
dc.titleUtility of the Ammonia-Free Birch Reduction of Electron-Deficient Pyrroles: Total Synthesis of the 20S Proteasome Inhibitor, clasto-Lactacystin b-Lactoneen_US
dc.typeArticleen_US


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