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Archive for the ‘Brooke rearrangement’ Category

Meerwein-Ponndorf-Verley followed by Brooke

Posted by naturalproductman on June 2, 2011

The Meerwein-Ponndorf-Verley reduction is the opposite of the Oppenauer oxidation.  Kei Takeda and co-workers from Hiroshima University have reported in ACIEE on a Meerwein-Ponndorf-Verley type reduction of an acyl silane followed by a Brooke rearrangement to afford siloxyallenes.  They were able to trap these allenes with a dienophile to undergo a [4+2] cycloaddition.

cycloaddition
ACIEE paper

Posted in Allenes, Asymmetric, Brooke rearrangement, Cascade Reactions, Cycloaddition, Diels-Alder, Meerwein-Ponndorf-Verley, Methodology, Named Reactions, Pericyclic reactions | Leave a Comment »

Synthesis of Prelaureatin

Posted by naturalproductman on May 12, 2010

Kei Takeda and co-workers at Hiroshima University have recently published in JOC on a diastereoselective Brooke rearrangement for the synthesis of prelaureatin.

prelaureatin


JOC paper

Posted in Brooke rearrangement, Cascade Reactions, Diastereoselective, Methodology, Named Reactions | Leave a Comment »

 
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