Naturalproductman’s Blog

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Archive for the ‘[2+2]’ Category

Asymmetric [2+2]

Posted by naturalproductman on November 15, 2013

Thorsten Bach and colleague have reported in Science on a Lewis acid catalyzed [2+2] reaction.

 

Science paper

Posted in Asymmetric, Cascade Reactions, Cycloaddition, Methodology, Pericyclic reactions, [2+2] | 1 Comment »

Gold catalyzed [2+2]

Posted by naturalproductman on March 20, 2013

Antonio Echavarren and co-workers from ICIQ in Spain have reported in Org Lett on a gold catalyzed intramolecular [2+2] between an alkene and alkyne.

[2+2]

OL paper

Posted in Cycloaddition, Gold, Methodology, Pericyclic reactions, Transition Metal, [2+2] | Leave a Comment »

That’s pretty strained

Posted by naturalproductman on February 20, 2013

Fumitoshi Kakiuchi and co-workers from Keio University have reported in Org Lett on a rhodium catalyzed [2+2] reaction between a terminal alkyne and an electron deficient alkene to form a cyclobutene.

strained

OL paper

Posted in Cycloaddition, Methodology, Rhodium, Transition Metal, [2+2] | Leave a Comment »

[2+2] by cationic gold

Posted by naturalproductman on October 17, 2012

Jose Gonzalez and co-workers from the University of Oviedo have reported in ACIE on a cationic gold catalyzed [2+2] reaction.

2+2

ACIE paper

Posted in Gold, Methodology, Transition Metal, [2+2] | Leave a Comment »

Jiadifenin synthesis

Posted by naturalproductman on August 29, 2012

Hongbin Zhai and co-workers at SIOC have reported in ACIE on the synthesis of jiadifenin.  The key [2+2] installed the methyl ester substituent.

jiadifenin synthesis

ACIE paper

Posted in Allenes, Cycloaddition, Methodology, Pericyclic reactions, Total Synthesis, [2+2] | Leave a Comment »

Acutimine approach

Posted by naturalproductman on August 15, 2012

Sarah Reisman and colleague have reported in Organic Letters on their elegant approach to acutimine via a [2+2] cycloaddition – however, their retro-aldol reaction to open the cyclobutane ring failed.

acutimine

OL paper

Posted in Alkaloids, Cycloaddition, Light Mediated, Methodology, Pericyclic reactions, [2+2] | Leave a Comment »

2 routes for elatenyne and is DFT going to be a standard for natural product structure assignment?

Posted by naturalproductman on July 3, 2012

Deukjoon Kim (Seoul National University) and Jonathon Burton (University of Oxford) and co-workers have reported in JACS on a synthesis of elatenyne.

elatenyne

JACS paper

Posted in Cascade Reactions, Methodology, Tetrahydrofuran, [2+2] | Leave a Comment »

Bielschowskysin core

Posted by naturalproductman on April 17, 2012

Johann Mulzer and co-workers at the University of Vienna have reported in Organic Letters on the synthesis of the tricyclic core of bielschowskysin.  Surprisingly, that cyclobutane with the five membered ring is stable in many different conditions (ie:  LiOH).

cyclobutane

OL paper

Posted in Cycloaddition, Cyclobutanes, Methodology, Pericyclic reactions, Polycyclic, [2+2] | Leave a Comment »

Thiophene and alkene

Posted by naturalproductman on February 29, 2012

Takeshi Ohkuma and co-workers at Hokkaido University have reported in Organic Letters on a light mediated intramolecular cyclization of a thiophene and an alkene.

cyclization

OL paper

Posted in Cascade Reactions, Light Mediated, Methodology, [2+2] | Leave a Comment »

Frondosin via Paterno Buchi

Posted by naturalproductman on February 29, 2012

Jonathan George and co-workers at the University of Adelaide have reported in Organic Letters on a Paterno Buchi reaction approach to access the 5 membered ring of frondosin.

Paterno Buchi

OL paper

Posted in Alkaloids, Cycloaddition, Light Mediated, Methodology, Named Reactions, Paterno-Buchi, Pericyclic reactions, [2+2] | Leave a Comment »

 
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