Naturalproductman’s Blog

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Archive for the ‘Stereochemistry’ Category

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 »

Chlorizidine A

Posted by naturalproductman on February 20, 2013

Chambers Hughes and co-workers at Scripps have reported in Organic Letters on the isolation of chlorizidine A, which had low micromolar LC50 values against some cancer cell lines from NCI. Another interesting point in this paper is the way they assigned the chiral carbon stereocenter as S from an X-ray crystal structure of the molecule, which also incorporated a benzene molecule. They determined the stereocenter using the Flack parameter.

chlorizidine A

OL paper

Flack parameter ref (Acta Cryst)

Posted in Alkaloids, breast, Cancer, melanoma, Stereochemistry | Leave a Comment »

Carbon-carbon coupling constants for stereochemical determination

Posted by naturalproductman on January 17, 2013

R. Thomas Williamson and co-workers at Merck have reported in Organic Letters on the use of DFT to calculate and assign stereochemistry from the C-C coupling constants in NMR.

NMR

OL paper

Posted in Alkaloids, Computational, DFT, Methodology, Stereochemistry | Leave a Comment »

Secondary alcohol stereochemistry

Posted by naturalproductman on April 17, 2012

Ion Ghiviriga at the University of Florida has reported in JOC on the use of NOESY1D to determine the stereochemistry of secondary alcohols by converting the alcohol to an MPA ester.

MPA

JOC paper

Posted in Methodology, New Setups, Stereochemistry | Leave a Comment »

 
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