Naturalproductman’s Blog

Hey, is that a natural product?!

Archive for the ‘Grob fragmentation’ Category

Grob Fragmentation for Daphnilongeranin B

Posted by naturalproductman on March 9, 2011

David Zhigang Wang and co-workers from Peking University have reported in Organic Letters on a Grob fragmentation approach to access the seven membered ring in daphnilongeranin B.

Grob

 

OL paper

Posted in Alkaloids, Cascade Reactions, Cycloaddition, Grob fragmentation, Light Mediated, Methodology, Named Reactions, Pericyclic reactions | Leave a Comment »

Vedelianin Synthesis

Posted by naturalproductman on March 6, 2011

David Wierner and colleague from the University of Iowa have reported in Tetrahedron Letters on the synthesis of vedelianin via an epoxide opening cascade.

epoxide

TL paper

Posted in Cascade Reactions, Grob fragmentation, Methodology, Named Reactions | Leave a Comment »

Grob Fragmentation to Subsituted Piperidines

Posted by naturalproductman on October 15, 2010

Andre Charette and co-worker at the University of Montreal in Canada have published in JOC on a Grob fragmentation approach to access a substituted piperidine, which in turn was used as a precursor for an indolizidine.

Grob fragmentation

 

JOC paper

Posted in Alkaloids, C-C Bond Breaking, Cascade Reactions, Grob fragmentation, Methodology, Named Reactions, Ring Opening | Leave a Comment »

Grob Fragmentation

Posted by naturalproductman on July 14, 2010

Alain Krief and co-workers have published in Tetrahedron Letters on cyclopropannelation/Haller-Bauer scission/Grob-fragmentation cascade reaction.

grob


TL paper

Posted in C-C Bond Breaking, Cascade Reactions, Grob fragmentation, Haller-Bauer scission, Methodology, Named Reactions | Leave a Comment »

R-Muscenone Synthesis

Posted by naturalproductman on January 19, 2010

Charles Fehr and co-workers at Firmenich SA, a company that specializes in fragrant and flavor chemicals, in Switzerland have recently published in Chemistry – A European Journal on the synthesis of R-muscenone.  They have successfully achieved an enantioselective Aldol reaction through dynamic kinetic resolution using an ephedrine alkoxide base.  A reduction of the Aldol adduct (beta-hydroxy ketone) and subsequent Grob fragmentation followed in order to access the Z-olefin in the macrocyle.

muscenone

Chemistry – A European Journal paper

Posted in C-C Bond Breaking, Grob fragmentation, Macrocycles, Methodology, Named Reactions, Ring forming, Ring Opening, Titanium, Transition Metal | Leave a Comment »

 
Follow

Get every new post delivered to your Inbox.

Join 71 other followers