Naturalproductman’s Blog

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Archive for the ‘Structural Reassignment’ Category

Why chemistry matters…

Posted by naturalproductman on May 22, 2014

Here’s a great example that was highlighted in C&E News illustrating why it is good to know chemistry and why people who are careful chemists/scientists are so valuable. The El-Deiry lab at Penn State had patented a compound they discovered with anti-cancer activity. Then the Janda group in Scripps had synthesized the structure and found it did not have the biological activity that was reported, and then they received the compound from NCI and it did have activity. The original structural assignment was incorrect as shown by X-ray crystallography. Now there’s a big issue.

 

ACIE paper

Posted in Structural Reassignment, Total Synthesis | Leave a Comment »

Posted by naturalproductman on July 21, 2013

Stephen Martin and co-workers have reported in JACS on a synthesis of citirnadin A.

citrinadin A

JACS paper

Posted in Alkaloids, Asymmetric, Methodology, Stereochemistry, Structural Reassignment, Total Synthesis | Leave a Comment »

Citrinadin B synthesis

Posted by naturalproductman on July 21, 2013

John Wood and co-workers at Colorado State University have reported in JACS on a synthesis of citrinadin.

alkaloid

JACS paper

Posted in Alkaloids, Cascade Reactions, Methodology, Stereochemistry, Structural Reassignment, Total Synthesis | Leave a Comment »

Roxbin B

Posted by naturalproductman on May 21, 2013

Hidetoshi Yamada and co-workers at Kwansei Gakuin University have reported in JOC on a structural reassignment concluding that roxbin B is cuspinin.

roxbin B

JOC paper

Posted in Glycosides, Methodology, Structural Reassignment, Total Synthesis | Leave a Comment »

Garuganin and garugamblin syntheses

Posted by naturalproductman on March 20, 2013

Chris Beaudry and co-workers at Oregon State have reported in JOC on some syntheses of diaryl heptanoids.

heptanoids

JOC paper

Posted in Asymmetric, Heptanoids, Mechanistic, Methodology, Structural Reassignment, Total Synthesis | Leave a Comment »

Haouamine B synthesis

Posted by naturalproductman on December 5, 2012

Dirk Trauner and co-workers have reported in JACS on the synthesis of haouamine B.

haouamine B

JACS paper

Posted in Alkaloids, Cascade Reactions, Methodology, Structural Reassignment, Total Synthesis | Leave a Comment »

Roxbin proposed structure??

Posted by naturalproductman on November 16, 2012

Hidetoshi Yamada and co-workers at Kwansei Gakuin have reported in Organic Letters on the proposed structure of roxbin.

roxbin

OL paper

Posted in Methodology, Structural Reassignment, Total Synthesis | Leave a Comment »

FD-895 synthesis

Posted by naturalproductman on October 25, 2012

Michael Burkart and James J. La Clair and colleagues at UCSD have reported in Org Lett on the synthesis of

synthesis
OL paper

Posted in Macrolides, Metathesis, Methodology, Polyketides, Ring forming, Ruthenium, Structural Reassignment, Transition Metal | Leave a Comment »

Incarviditone synthesis

Posted by naturalproductman on September 7, 2012

Yefeng Tang and co-workers at Tsinghua University have reported in Organic Letters on their synthesis of incarviditone.

incarviditone

OL paper

Posted in Cascade Reactions, Dimer, Methodology, Structural Reassignment, Total Synthesis | Leave a Comment »

Phomopsichalasin is actually diaporthichalasin

Posted by naturalproductman on July 2, 2012

Thomas Hoye and co-workers from the University of Minnesota have reported in the Journal of Natural Products on the structural reassignment of a natural product using DFT to calculate the NMR chemical shifts.

DFT

JNP paper

Posted in Alkaloids, Computational, DFT, Structural Reassignment | Leave a Comment »

 
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