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Archive for the ‘Claisen rearrangement’ Category

Claisen-Diels-Alder cascade to spirooliganones A and B

Posted by naturalproductman on July 16, 2014

Rongbiao Tong and co-workers from the Hong Kong University of Science and Technology have reported in Org Lett on a slick reaction to form spirooliganones.

 
spirooliganones

OL paper

Posted in Cascade Reactions, Claisen rearrangement, Diels-Alder, Methodology, Named Reactions, Total Synthesis | Leave a Comment »

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 »

Transtaganolide syntheses

Posted by naturalproductman on May 17, 2013

Brian Stoltz and co-workers have reported in ACIE on the syntheses of transtaganolides through an Ireland-Claisen rearrangement/Diels-Alder cascade.

ICR/DA

ACIE paper

Posted in Asymmetric, Cascade Reactions, Claisen rearrangement, Diels-Alder, Methodology, Named Reactions, Sesquiterpenes, Total Synthesis | Leave a Comment »

Rh-cascade

Posted by naturalproductman on April 22, 2013

Ken Tanaka and co-workers at the Tokyo University of Agriculture and Technology have reported in Org Lett on a rhodium catalyzed cascade reaction to yield substituted cyclopentanones.

rh

OL paper

Posted in Cascade Reactions, Claisen rearrangement, Methodology, Named Reactions, Rhodium, Transition Metal | Leave a Comment »

Vinigrol synthesis

Posted by naturalproductman on January 19, 2012

Louis Barriault and co-workers at the University of Ottawa have reported in ACIEE on the formal synthesis of vinigrol – I think this makes the number of groups to synthesize this molecule to 2, Baran being the other one.

vinigrol

ACIEE paper

Posted in Cascade Reactions, Claisen rearrangement, Diels-Alder, Methodology, Named Reactions, Total Synthesis | Leave a Comment »

Lysidicin A synthesis from a triple Claisen rearrangement

Posted by naturalproductman on January 17, 2012

Hidenori Watanabe and co-workers at the University of Tokyo have reported in Tetrahedron on the synthesis of lysidicin.  The key reaction being a triple Claisen rearrangement that formed three of the aryl carbon bonds from aryl ether linkages.

Claisen

Tetrahedron paper

Posted in Cascade Reactions, Claisen rearrangement, Methodology, Mitsunobu, Named Reactions, Polyketides, Total Synthesis | Leave a Comment »

Saudin synthesis

Posted by naturalproductman on November 21, 2011

Robert Boeckman and co-workers at the University of Rochester have reported in Tetrahedron on the synthesis of saudin.

saudin

Tetrahedron paper

Posted in Asymmetric, Cascade Reactions, Claisen rearrangement, Methodology, Named Reactions, Terpenes | Leave a Comment »

Transannular Claisen rearrangement

Posted by naturalproductman on October 23, 2011

Donald Craig and co-workers at Imperial College have reported in Organic and Biomolecular Chemistry on a transannular Claisen rearrangement converting a lactone into a cyclobutane.

Claisen

OBC paper

Posted in Claisen rearrangement, Methodology, Named Reactions, Ring contraction | Leave a Comment »

Daphmanidin synthesis

Posted by naturalproductman on October 11, 2011

Erick Carreira and co-worker have reported in ACIEE on the synthesis of daphmanidin.

daphmanidin

ACIEE paper

Posted in Alkaloids, Cascade Reactions, Claisen rearrangement, Cobalt, Copper, cross coupling, Heck, Methodology, Named Reactions, Palladium, Transition Metal | Leave a Comment »

Alkyne to caged compound

Posted by naturalproductman on June 9, 2011

Qi-Dong You and co-workers from China Pharmaceutical University have reported in Tetrahedron on a diyne compound undergoing a hydrogenation/Claisen/Diels-Alder cascade to afford the caged carbon skeleton of gaudichaudione A and isomorellin.

palladium

Tetrahedron paper

Posted in Cascade Reactions, Claisen rearrangement, Diels-Alder, Methodology, Named Reactions, Palladium, Transition Metal | Leave a Comment »

 
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