Literature DB >> 20704267

Catalyst-controlled formal [4 + 3] cycloaddition applied to the total synthesis of (+)-barekoxide and (-)-barekol.

Yajing Lian1, Laura C Miller, Stephen Born, Richmond Sarpong, Huw M L Davies.   

Abstract

The tandem cyclopropanation/Cope rearrangement between bicyclic dienes and siloxyvinyldiazoacetate, catalyzed by the dirhodium catalyst Rh(2)(R-PTAD)(4), effectively accomplishes enantiodivergent [4 + 3] cycloadditions. The reaction proceeds by a cyclopropanation followed by a Cope rearrangement of the resulting divinylcyclopropane. This methodology was applied to the synthesis of (+)-barekoxide (1) and (-)-barekol (2).

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Year:  2010        PMID： 20704267      PMCID： PMC3033432          DOI： 10.1021/ja103916t

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  11 in total

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Review 5.  Modern synthetic efforts toward biologically active terpenes.

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  20 in total

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8.  Rhodium-catalyzed enantioselective vinylogous addition of enol ethers to vinyldiazoacetates.

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9.  Divergent outcomes of carbene transfer reactions from dirhodium- and copper-based catalysts separately or in combination.

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