Naturalproductman’s Blog

Hey, is that a natural product?!

Archive for the ‘Terpenes’ 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 »

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.

taiwaniadducts

JACS paper

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.

decaturin C

Tetrahedron paper

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.

tetraterpenes

Tetrahedron paper

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.
manoalide

JNP paper

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.

Diels Alder

OL paper

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.

saudin

Tetrahedron paper

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).

C35

JACS paper

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.

synthesis

TL paper

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.

taiwaniaquinone

Chemistry – a European Journal paper

Posted in Cascade Reactions, Methodology, Ring contraction, Terpenes | Leave a Comment »