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!
Archive for the ‘Terpenes’ Category
Mechanistic insights towards endoperoxide formation of artemisinin
Posted by naturalproductman on June 17, 2021
Posted in Antimalarial, Cyclic Peroxides, Diseases, Isotope effects, Malaria, Mass Spectrometry, Mechanistic, Peroxides, Terpenes | Leave a Comment »
Taiwaniadducts B, C, and D syntheses
Posted by naturalproductman on June 3, 2014
Ang Li and co-workers from SIOC have reported in JACS on the syntheses of taiwaniadducts B, C, and D.
Posted in Europium, Lanthanides, Methodology, Terpenes, Terpenoids, Total Synthesis | Leave a Comment »
Decaturin C synthesis
Posted by naturalproductman on September 19, 2012
Hirosato Takikawa and co-workers at Kobe University have reported in Tetrahedron on the synthesis of decaturin C, a compound with insecticidal properties. I was curious about the hemiketal formation – whether or not the hemiketal is formed completely or it is in equilibrium with the ketone.
Posted in Methodology, Polyketides, Terpenes, Total Synthesis | Leave a Comment »
Abiestetranes A and B
Posted by naturalproductman on August 6, 2012
Wei-Dong Zhang and co-workers from have reported in Tetrahedron on the isolation of some spirocyclic tetraterpenes, abiestetranes A and B.
Posted in Cancer, Spirocycles, Terpenes | Leave a Comment »
Manoalide vs. HCV
Posted by naturalproductman on March 30, 2012
Nobuyoshi Akimitsu and co-workers from the University of Tokyo have reported on the identification of manoalide A as an inhibitor for heptatitis C virus NS3 helicase.
Posted in Diseases, Enzymes, Hepatitis C, Protein Targets, Proteins, Terpenes | Leave a Comment »
Anisatin synthesis
Posted by naturalproductman on February 29, 2012
Tohru Fukuyama and co-workers have reported in Organic Letters on the synthesis of anisatin via a Diels-Alder.
Posted in Diels-Alder, Methodology, Named Reactions, Terpenes | Leave a Comment »
Saudin synthesis
Posted by naturalproductman on November 21, 2011
Robert Boeckman and co-workers at the University of Rochester have reported in Tetrahedron on the synthesis of saudin.
Posted in Asymmetric, Cascade Reactions, Claisen rearrangement, Methodology, Named Reactions, Terpenes | Leave a Comment »
A new C35-terpene cyclase
Posted by naturalproductman on June 7, 2011
Tsutomu Sato and co-workers from Niigata University have reported in JACS on the identification of a terpene cyclase enzyme that cyclized a C35 terpene (sesquarterpene).
Posted in Chemical Biology, Enzymatic, Methodology, Sesquarterpenes, Terpenes | Leave a Comment »
Epi-cochlioquinone A Synthesis
Posted by naturalproductman on September 20, 2010
Kuniaki Tatsuta and co-workers from Waseda University have published in Tetrahedron Letters on a total synthesis of epicochlioquinone A featuring a vinylogous Michael reaction and many more.
Posted in Cascade Reactions, Cycloaddition, Methodology, Michael, Named Reactions, Pericyclic reactions, Terpenes | Leave a Comment »
A Ring Contraction Approach for Taiwaniaquinone
Posted by naturalproductman on June 14, 2010
Karl Gademann and co-workers at the University of Basel in Switzerland have published in a ring contraction approach – an intramolecular benzilic acid rearrangement – to access the taiwaniaquinone carbon skeleton.
Posted in Cascade Reactions, Methodology, Ring contraction, Terpenes | Leave a Comment »