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Archive for the ‘Peroxides’ Category

Mechanistic insights towards endoperoxide formation of artemisinin

Posted by naturalproductman on June 17, 2021

Artemisinin, one of the topics of the Nobel Prizes in Medicine in 2015, and its derivatives have been used to treat malaria. A new study published in the Journal of Natural Products finds that the endoperoxide formation of artemisinin from dihydroartemisinic acid, its biosynthetic precursor, undergoes a mixed mechanism. The study, from the lab of Francis Yoshimoto at UTSA, used regioselectively deuterated dihydroartemisinic acid isotopologues to measure competitive intermolecular kinetic isotope effects in the formation of artemisinin. The supporting information file is over 500 pages!

Cool!


Journal of Natural Products
paper

Posted in Antimalarial, Cyclic Peroxides, Diseases, Isotope effects, Malaria, Mass Spectrometry, Mechanistic, Peroxides, Terpenes | Leave a Comment »

How to make an endoperoxide

Posted by naturalproductman on January 18, 2015

Yikang Wu and colleague at SIOC have reported in Organic Letters on an interesting epoxy-olefin rearrangement to access endoperoxides.

endoperoxide

OL paper

Posted in Cascade Reactions, Methodology, Peroxides | Leave a Comment »

Cardamom peroxide synthesis

Posted by naturalproductman on March 27, 2014

Thomas Maimone and co-worker from UC Berkeley have reported in JACS on a 4-step synthesis of cardamom peroxide from myrtenal.

 

 

JACS paper

Posted in Diseases, Malaria, Peroxides, Total Synthesis | Leave a Comment »

Gracilioether H has anti-malarial activity

Posted by naturalproductman on October 23, 2012

Angela Zampella and co-workers have reported in Tetrahedron on the isolation of gracilioethers.  Gracilioether H had anti-malarial activity.

gracilioether H

Tetrahedron paper

Posted in Diseases, Malaria, Methodology, Peroxides | Leave a Comment »

[2+2+2] for endoperoxides

Posted by naturalproductman on February 29, 2012

Tehshik Yoon and co-workers at the University of Wisconsin have reported in Organic Letters on a [2+2+2] cyclization approach to form endoperoxides using oxygen (ie:  O2).

O2

OL paper

Posted in Cascade Reactions, Light Mediated, Methodology, Peroxides, Ruthenium, Transition Metal | Leave a Comment »

Catharoseumine

Posted by naturalproductman on February 20, 2012

Xiao-Jiang Hao and co-workers from the Kunming Institute of Botany have reported in Tetrahedron Letters on the isolation of catharoseumine a peroxy containing alkaloid.

peroxide

TL paper

Posted in Alkaloids, Indoles, Monoterpenoids, Peroxides | Leave a Comment »

Cyclic peroxides from triketones

Posted by naturalproductman on February 10, 2012

Alexander Terent’ev and co-workers from the Russian Academy of Sciences have reported in JOC on a method to form cyclic peroxides from triketones.

cyclic peroxides

JOC paper

Posted in Cascade Reactions, Methodology, Peroxides | Leave a Comment »

Merulin C lowers phosphorylation of Erk1/2

Posted by naturalproductman on October 15, 2011

Khanitha Pudhom and co-workers have reported in the Journal of Natural Products on the isolation and activity of some endoperoxides from a Thai mangrove derived fungus.

Erk1/2

JNP paper

Posted in Cancer, Diseases, Enzymes, Peroxides, Proteins | Leave a Comment »

Talaperoxides

Posted by naturalproductman on May 6, 2011

Zhigang She and co-workers Sun-yat Sen University have reported in the Journal of Natural Products on the isolation of talaperoxides, norsesquiterpene peroxides.

talaperoxides

JNP paper

Posted in Cancer, Norsesquiterpenes, Peroxides | Leave a Comment »

Epiplakinidioic Acid

Posted by naturalproductman on October 11, 2010

Abimael Rodriguez and co-workers from the University of Puerto Rico have published in the Journal of Natural Products on the isolation of epiplakinidioic acid, which had an IC50 value of 0.3 micromolar against Plasmodium falciporum.

peroxide

 

JNP paper

Posted in Diseases, Malaria, Peroxides, Polyenes, Polyketides | Leave a Comment »