Naturalproductman’s Blog

Hey, is that a natural product?!

Biochemometric analysis ~ natural products (altersetin)

Posted by naturalproductman on February 9, 2016

Nadja Cech and co-workers at UNC Greensboro have reported in the Journal of Natural Products on the isolation of altersetin, an antibacterial alkaloid.

 

JNP paper

Posted in Alkaloids, Antibiotics, New Techniques | Leave a Comment »

Peniherquamide C

Posted by naturalproductman on February 9, 2016

Fumio Sugawara and co-workers from the Tokyo University of Science have reported in the Journal of Natural Products on the isolation of peniherquamide C, which had anti-hepatitis C virus activity (IC50 value of 5.1 μM).

 

JNP paper

Posted in Alkaloids, Antiviral | Leave a Comment »

Why natural products are important (an update)

Posted by naturalproductman on February 9, 2016

Remember that natural products review by David Newman and Gordon Cragg from the NIH?

 

Here is an updated (2016) one covering new chemical entities, antibacterial, antifungal, antiviral, anticancer, antiparasitic, and anticancer from 1981 to 2014:

 

JNP paper

Posted in Cancer, Random, Unnatural Products | Leave a Comment »

Nuphar alkaloid chemical biology

Posted by naturalproductman on February 8, 2016

Jimmy Wu and co-workers reported in ACIE on the formal synthesis of nuphar alkaloids and their apoptotic activity. Did you know that the second “p” in “apoptosis” is silent and it is pronounced “apa-tosis”? The Greek word “apoptosis” means “falling off” or “dropping off” of flower petals or tree leaves.

 

ACIE paper

Posted in Chemical Biology, Random, Unnatural Products | 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 »

Strictamine synthesis

Posted by naturalproductman on February 4, 2016

Jieping Zhu and co-workers reported in ACIE on the synthesis of strictamine.

 

ACIE paper

Posted in Indoles, Total Synthesis | 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 »

Gold catalyzed photoredox chemistry

Posted by naturalproductman on February 3, 2016

Stephen Hashmi and co-workers have reported in ACIE on the use of a gold dimer catalyst with a diphenylphosphinomethane ligand to effect a difluoroalkylation reaction.

hashmi ACIE 2016.gif

ACIE paper

Posted in Gold, Light Mediated, Methodology, Radical Chemistry, Transition Metal | Leave a Comment »

A review of total synthesis and prospects for the future

Posted by naturalproductman on February 3, 2016

Larry Overman and co-workers have reported in ACIE on a nice review of 12 elegant examples of total synthesis of natural products bearing 2 or more quaternary carbon centers bonded to each other. I like that it is a nice “cliff notes” version of a lot of great work.

 

ACIE paper

Posted in Random, Total Synthesis | Leave a Comment »

Nahuoic acid

Posted by naturalproductman on February 3, 2016

Raymond Andersen and co-workers reported in JOC on the isolation of nahuoic acid. They used Rychnovsky’s method to determine the relative stereochemistry of the alcohols.

 

JOC paper

Posted in Cancer, Classic papers, Classical rules, Polyketides, Protein Targets, Rycnovsky's rules | Leave a Comment »

 
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