Naturalproductman’s Blog

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Archive for the ‘Polyketides’ Category

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 »

Sanggenons C and O syntheses

Posted by naturalproductman on January 19, 2016

John Porco and co-workers at Boston University have reported in JACS on the syntheses of sanggenons C and O.

 

JACS paper

Posted in Diels-Alder, Named Reactions, Polyketides, Total Synthesis | Leave a Comment »

Shapeshifting natural product

Posted by naturalproductman on November 27, 2015

John Porco and co-workers reported in JACS on the synthesis of a shapeshifting natural product, secalonic acid A. When I think of shapeshifting molecules, I think of Jeffrey Bode’s work with unnatural compounds, but I did not realize that natural products are also known to shape shift.

NATURALPRODUCTMAN 11.28.2015.gif

JACS paper

Posted in Polyketides, Total Synthesis | Leave a Comment »

Got wood?

Posted by naturalproductman on October 21, 2015

Till Opatz and co-workers at Institut für Organische Chemie reported in ACIE on the synthesis of from compounds from wood – methyl gallate, ferulic acid, and methanol.
wood
ACIE paper

Posted in Polyketides, Total Synthesis | Leave a Comment »

Unciaphenol – Bergman cyclization product of uncialamycin

Posted by naturalproductman on October 16, 2015

Raymond Anderson and co-workers at the University of British Columbia report in Organic Letters on unciaphenol, which has anti-HIV activity.

unciaphenol

OL paper

Posted in Alkynes, Cascade Reactions, Diseases, HIV, Named Reactions, Polyketides | Leave a Comment »

Marmycin A synthesis

Posted by naturalproductman on October 13, 2015

Raphael Rodriguez and co-workers at CNRS UMR have reported in Nature Chemistry on the synthesis of marmycin A.

Nature Chemistry paper

Posted in Chemical Biology, Polyketides, Total Synthesis | Leave a Comment »

Going from a diol to a tetrahydropyran in salinomycin

Posted by naturalproductman on September 25, 2015

Peter Leadlay and co-workers from the University of Cambridge have reported in ACIE on the enzyme that makes the tetrahydropyran ring in salinomycin. The tetrahydropyran is proposed to come from a diol where one of the hydroxy groups is in the beta-position to a ketone and subsequently dehydrates to form an enone. The enone undergoes an intramolecular Michael reaction to form the tetrahydropyran. However, when the reaction is done in vitro with the purified enzyme, they don’t see the enone intermediate, so I wonder if it is a processive reaction; in other words, the enone forms in the enzyme active site without being released and cyclizes to the tetrahydropyran.

salinomycin

ACIE paper

Posted in Biosynthesis, Chemical Biology, Enzymes, Mechanistic, Polyketides, Tetrahydropyran | Leave a Comment »

Rubriflordilactone A synthesis

Posted by naturalproductman on September 2, 2015

Edward Anderson and co-workers from the University of Oxford have reported in ACIE on the synthesis of rubriflordilactone A.

lactone

ACIE paper

Posted in Lactones, Polyketides, Total Synthesis | Leave a Comment »

Pericoannosin A

Posted by naturalproductman on August 27, 2015

Jungui Dai and co-workers from Chinese Academy of Medical Sciences have reported in Organic Letters on the isolation of pericoannosin A.

funal

OL paper

Posted in Antiviral, Polyketides | Leave a Comment »

Griseusin synthesis

Posted by naturalproductman on August 20, 2015

Jon Thorson and co-workers from the University of Kentucky have reported in ACIE on the syntheses of griseusins.
griseusins
ACIE paper

Posted in C-H activation, Methodology, Polyketides, Total Synthesis | Leave a Comment »

 
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