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Archive for the ‘Computational’ Category

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 »

[6+4] vs [4+2]

Posted by naturalproductman on October 16, 2015

Kendall Houk and co-workers have reported in JACS on a biosynthetic study of heronamide A using DFT calculations to study the [6+4] cycloaddition.

6+4

JACS paper

Posted in Biosynthesis, Cycloaddition, DFT | Leave a Comment »

Correlating chemical shift of O-H proton with stereochemistry of masked 1,2-diols

Posted by naturalproductman on October 9, 2015

Jason Chen and co-workers from Iowa State have reported in JOC on the chemical shifts of an O-H proton of masked syn- and anti- 1,2-diols.

NMR

JOC paper

Posted in Computational, DFT, New Setups, NMR, Stereochemistry | Leave a Comment »

Evans enolate in solution

Posted by naturalproductman on October 5, 2015

David Collum and colleague have reported in JACS on the solution structure of an Evans enolate.
Evans

JACS paper

Posted in Computational, DFT, Mechanistic, Methodology | Leave a Comment »

Mechanistic study of the asymmetric Nazarov cyclization

Posted by naturalproductman on October 1, 2015

Kendall Houk and co-workers reported in JACS on a mechanistic investigation on a reaction discovered by Tius: the asymmetric Nazarov cyclization catalyzed by a thiourea-primary amine catalyst.

DFT

JACS paper

Posted in Computational, DFT, Mechanistic, Named Reactions, Nazarov cyclization | Leave a Comment »

Mollenynes B-E

Posted by naturalproductman on September 25, 2015

Tadeusz Molinski and co-workers have reported in JACS on the isolation and characterization of mollenynes B-E.
mollenynes
JACS paper

Posted in Alkynes, Computational, DFT, Halogenated, New Techniques, NMR, Peptides, Polyenes, Stereochemistry | Leave a Comment »

Triazoline + light

Posted by naturalproductman on September 4, 2015

Miguel Garcia-Garibay and co-workers at UCLA have reported in Organic Letters on a denitrogenation reaction of a triazoline using light to make an aziridine.
triazole
OL paper

Posted in Computational, Light Mediated, Mechanistic, Methodology | Leave a Comment »

Diels-Alder approach to galbulimima alkaloids

Posted by naturalproductman on August 25, 2015

Here’s a paper related to the galbulimima alkaloids, which were made famous by Lewis Mander’s group. Regan Thomson and co-workers report in JACS on the synthesis of galbulimima alkaloids. A nice collaboration with DFT calculations from Dean Tantillo’s group shows the orbital interactions in the transition state structures of the Diels-Alder reactions.
galbulimima

JACS paper

Posted in Alkaloids, DFT, Diels-Alder, Methodology, Total Synthesis | Leave a Comment »

Welcome to the future

Posted by naturalproductman on August 7, 2015

I read the title of this paper and immediately thought of David Baker’s work. I guess we are getting closer to having a logical approach available to design our own protein catalysts.
design
JACS paper

Posted in Computational, Enzymes, Methodology | 2 Comments »

Newman-Kwart reaction mechanism

Posted by naturalproductman on July 13, 2015

Hafize Ozcan and co-workers from Trakya University in Turkey have reported in Tetrahedron on an interesting mechanistic investigation of the Newman-Kwart reaction.

Newman-Kwart

Tetrahedron paper

Posted in Cascade Reactions, Computational, DFT, Electrocyclization, Mechanistic, Methodology, Named Reactions, Newman-Kwart, Sigmatropic Rearrangements | Leave a Comment »

 
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