Naturalproductman’s Blog

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Archive for the ‘Mechanistic’ Category

From vinyl azides to alpha-fluoroketones

Posted by naturalproductman on July 31, 2016

Feng Liu and colleague at Soochow University reported in Organic Letters on using Selectfluor to convert vinyl azides to alpha-fluoroketones.

 

OL paper

Posted in Cascade Reactions, Mechanistic, Methodology | Leave a Comment »

Mechanism of hexadehydro Diels Alder

Posted by naturalproductman on June 16, 2016

Thomas Hoye and co-workers reported in JACS on a substituent effect on the rate of the hexadehydro-Diels Alder reaction. Unlike the regular Diels-Alder reaction, electron-withdrawing groups slowed the reaction down suggesting a step-wise diradical mechanism as opposed to a concerted mechanism.

 

JACS paper

Posted in Cascade Reactions, Mechanistic, Methodology | Leave a Comment »

From a dithiane-vinyl chloride to furan

Posted by naturalproductman on April 19, 2016

Shouchu Tang and co-workers from Lanzhou University have reported in Organic Letters on an interesting transformation that undergoes an allene intermediate.

 

OL paper

Posted in Cascade Reactions, Mechanistic, Methodology | Leave a Comment »

Enyne metathesis – a mechanistic investigation

Posted by naturalproductman on April 14, 2016

Steven Diver and co-workers at SUNY Buffalo have reported in JACS on a mechanistic study of enyne metathesis using Hoveyda catalyst and Grubbs 2nd generation catalyst.

 

JACS paper

Posted in Kinetics, Mechanistic, Methodology, Ruthenium, Transition Metal | Leave a Comment »

Olefin difluorination

Posted by naturalproductman on April 5, 2016

Eric Jacobsen and co-workers reported in JACS on a difluorination of an olefin. They accomplished this transformation by using mCPBA (1.1 equivalent), HF-pyridine (100 equivalents of HF), and an aryl iodide derivative (catalyst).

 

JACS paper

Posted in Hypervalent Iodine, Mechanistic, Methodology | Leave a Comment »

[4+2] with diazo esters

Posted by naturalproductman on February 8, 2016

Michael Doyle and co-workers at UT San Antonio have reported in JACS on the first Diels-Alder example involving a diazoester dienophile.

DOYLE jacs 2016

JACS paper

Posted in Cascade Reactions, Mechanistic, Methodology | Leave a Comment »

The enamine is formed through an oxazolidinone intermediate

Posted by naturalproductman on February 4, 2016

When I think of organocatalysis, I usually think of a carbonyl compound forming an enamine intermediate, which in turn attacks an electrophile. The enamine is usually formed when the carbonyl compound reacts with a proline-derived catalyst. By using Gaussian and experimental KIE calculations, Matthew Vetticatt and co-workers at Binghamton University reported in JACS on the way that the enamine compound is formed: through an oxazolidinone intermediate.

oxazolidinone

JACS paper

 

A review article on determining the transition state structures based on KIEs.

Posted in Computational, Isotope effects, Mechanistic | Leave a Comment »

2 Reagents, 2 mechanisms, same product

Posted by naturalproductman on January 28, 2016

Srinivasan Chandrasekaran and colleague at the Indian Institute of Science have reported in Tetrahedron on a mechanistically interesting transformation involving a geminal aminooxygenation of a vinyl arene. Two different reaction conditions were identified: one with m-CPBA, the other with a hypervalent iodine reagent. The former underwent a deuterium shift on the gem-dideuterated-styrene starting material and the latter does not.

01.28.2016 naturalproductman.gif

Tetrahedron paper

Posted in Cascade Reactions, Hypervalent Iodine, Mechanistic, Methodology | Leave a Comment »

JOC papers of interest 11/24/2015

Posted by naturalproductman on November 24, 2015

James White and co-workers reported on the synthesis of Huperzine A.

Christopher Marvin and co-workers from Hendrix College reported in JOC on the synthesis of tetrabenazine through a photoredox reaction to afford the piperidone moiety.

Young-Ger Suh and co-workers from Seoul National University reported on the synthesis of galiellalactone.

Ronaldo Pilli and co-workers from  Universidad Estadualde Campinas have reported on the synthesis of cryptomoscatone E3.

Scott Denmark and colleague reported on an asymmetrice 2,3-Wittig rearrangement.

JOC 11.24.2015 FKY

Posted in Alkaloids, Light Mediated, Mechanistic, Methodology, Sigmatropic Rearrangements, Total Synthesis | Leave a Comment »

From gene clusters to biosynthesis of natural products

Posted by naturalproductman on October 16, 2015

Leadlay (University of Cambridge) and Sun (Wuhan University) and co-workers have reported in Chemical Science on thiotetronate biosynthesis.

gene

Chemical Science paper

Posted in Biosynthesis, Mechanistic, Thiotetronate | Leave a Comment »

 
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