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Archive for the ‘Cope rearrangement’ Category

Ireland Claisen/Cope rearrangement

Posted by naturalproductman on June 30, 2014

James Leighton and co-workers reported in JACS on a mechanistic study of a tandem Ireland Claisen/Cope rearrangement reaction to form some polycyclic rings.

oxy Cope

JACS paper

Posted in Cascade Reactions, Claisen rearrangement, Cope rearrangement, Mechanistic, Methodology, Named Reactions, oxy-Cope rearrangement | Leave a Comment »

Reaction after another

Posted by naturalproductman on September 25, 2011

Corey Stephenson and colleague at Boston University have reported in Organic Letters on an iridium catalyzed tandem reaction using visible light – the reaction forms a divinyl cyclopropane intermediate that undergoes a Cope rearrangement.

cascade

OL paper

Posted in Cascade Reactions, Cope rearrangement, Iridium, Methodology, Named Reactions, Ring expansion, Ring forming, Transition Metal | Leave a Comment »

Vittatalactone Synthesis

Posted by naturalproductman on January 31, 2011

Christoph Schneider and co-workers at Universitat Leipzig have published in Chem Comm on their total synthesis of vittatalactone, which involves an oxy-Cope rearrangement to place the carbons in the correct position with unsaturation followed by an asymmetric reduction to yield the methyls in the correct stereochemical arrangement.

vittatalactone

 

Chem Comm paper

Posted in Cascade Reactions, Cope rearrangement, Iridium, Methodology, Named Reactions, oxy-Cope rearrangement, Pericyclic reactions, Sigmatropic Rearrangements, Transition Metal | Leave a Comment »

Gold Catalyzed Cycloheptannulation

Posted by naturalproductman on December 8, 2010

Cristina Nevado and co-workers from the Universitat Zurich in Switzerland have published in ACIEE on a gold catalyzed cycloheptannulation approach to accessing the seven membered ring in frondosin.

frondosin

 

ACIEE paper

Posted in Cascade Reactions, Cope rearrangement, Gold, Methodology, Named Reactions, Ring expansion, Seven-Membered Rings, Transition Metal | Leave a Comment »

[4+3] with Rhodium

Posted by naturalproductman on August 12, 2010

Richmond Sarpong and Huw Davies teamed up to published in JACS on a [4+3] cycloaddition approach to synthesize barekoxide and barekol using a dirhodium catalyst.

seven membered rings

JACS paper

Posted in Cascade Reactions, Cope rearrangement, Methodology, Named Reactions, Rhodium, Seven-Membered Rings, Transition Metal | Leave a Comment »

Cope Rearrangement to Seven Membered Rings

Posted by naturalproductman on June 29, 2010

Seven membered rings are hard to make but Vladimir Birman and co-workers at Washington University have published in Organic Letters on a [3,3] Cope rearrangement approach to access seven membered rings.

seven

OL paper

Posted in Cascade Reactions, Cope rearrangement, Methodology, Named Reactions, Pericyclic reactions, Ring forming, Sigmatropic Rearrangements | Leave a Comment »

 
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