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Archive for the ‘Sesquiterpenoids’ Category

Dihydroartemisinic Acid to Artemisinin

Posted by naturalproductman on December 20, 2019

Francis Yoshimoto and co-workers at the University of Texas at San Antonio (UTSA) have reported in the Journal of Natural Products on the synthesis of a dihydroartemisinic acid isotopologue, which was regioselectively deuterated at C-3, and in turn was used to measure the rate of nonenzymatic conversion to artemisinin. Artemisinin was the topic of the 2015 Nobel Prize in Medicine and the biosynthesis of the endoperoxide, which is responsible for its antimalarial activity, has been controversial. This paper is related to the spontaneous oxidation of dihydroartemisinic acid to artemisinin when a dried down sample of dihydroartemisinic acid was exposed to air. Funny enough, there is another article on the spontaneous oxidation of avermectin, which was the topic of the 2015 Nobel Prize in Medicine as well.

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J. Nat. Prod. paper (Artemisinin)

Posted in Antimalarial, Sesquiterpenoids | Leave a Comment »

Nitadisin synthesis

Posted by naturalproductman on June 28, 2014

Dirk Trauner and co-workers at Ludwig-Maximilians-Universität München have reported in ACIE on the synthesis of nitadisin.

nitadisin

ACIE paper

Posted in Sesquiterpenoids, Total Synthesis | Leave a Comment »

Frondosins A and B syntheses

Posted by naturalproductman on March 10, 2014

Dennis Wright and co-workers from the University of Connecticut have reported in JACS on the syntheses of frondosins A and B.

frondosin

JACS paper

Posted in Asymmetric, Methodology, Sesquiterpenoids, Total Synthesis | Leave a Comment »

Englerin synthesis

Posted by naturalproductman on August 28, 2012

Susumi Hatakeyama and co-workers at Nagasaki University have reported in JOC on the synthesis of englerin.

englerin

JOC paper

Posted in Asymmetric, Methodology, Sesquiterpenoids | Leave a Comment »

Presilphiperfolan-1-ol synthesis

Posted by naturalproductman on August 23, 2012

Stoltz and colleague have reported in ACIE on the enantioselective syntheses of some sesquiterpenoid biosynthetic precursors.  The 5,6-ring system was made from an intramolecular Diels-Alder.

biosynthetic

ACIE paper

Posted in Asymmetric, Cycloaddition, Diels-Alder, Methodology, Named Reactions, Pericyclic reactions, Sesquiterpenoids, Total Synthesis | Leave a Comment »

A Heck reaction for a seven membered ring

Posted by naturalproductman on June 11, 2012

Silas Cook and colleague at Indiana University have reported in Organic Letters on a formal synthesis of englerin.
englerin

OL paper

Posted in cross coupling, Heck, Methodology, Sesquiterpenoids, Seven-Membered Rings | Leave a Comment »

Englerin A formal synthesis

Posted by naturalproductman on May 7, 2012

Kathlynn Parker and colleague have reported in Organic Letters on a formal synthesis of englerin A.

englerin

OL paper

Posted in Cascade Reactions, Metathesis, Methodology, Ruthenium, Sesquiterpenoids, Transition Metal | Leave a Comment »

Chlorinated englerins

Posted by naturalproductman on February 10, 2012

John Beutler and co-workers from the NCI have reported in the Journal of Natural Products on the isolation of chlorinated englerins and their anti-cancer activities.

chlorinated

JNP paper

Posted in Cancer, renal, Sesquiterpenes, Sesquiterpenoids | Leave a Comment »

Tormesol via Wittig

Posted by naturalproductman on November 21, 2011

Dongjoo Lee and co-workers at Dankook University have reported in Tetrahedron on the synthesis of tormesol.  The seven membered ring was acquired from a Horner-Wadsworth-Emmons reaction.

Wittig

Tetrahedron paper

Posted in Horner-Wadsworth-Emmons, Methodology, Named Reactions, Named Reagents, Sesquiterpenoids, Total Synthesis, Wittig | Leave a Comment »

Compounds from a fungus

Posted by naturalproductman on October 8, 2011

Nicholas Oberlies and co-workers at UNC Greensboro have reported in the Journal of Natural Products on the isolation of some peptides and sesquiterpenoids from the terrestrial filamentous fungus, Trichothecium sp.

fungus

JNP paper

Posted in Depsipeptides, Polyenes, Sesquiterpenoids | Leave a Comment »