Naturalproductman’s Blog

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Archive for the ‘Diterpene’ Category

Enhancing water solubility of a drug (triptolide)

Posted by naturalproductman on November 25, 2015

Gunda Georg and co-workers at the University of Minnesota reported in the Journal of Medicinal Chemistry on the addition of a phosphonooxymethyl group onto triptolide to increase its water solubility by greater than 3,580 times. (slight mistake: Scheme 2 in the paper has the use of benzoyl peroxide shown as “Bn2O2” when it should be “Bz2O2” – Bn2O2 would be benzyl peroxide). Another interesting point from this paper is that this natural product has multiple modes of action where it can covalently attach to proteins (XPB, xeroderma pigmentosum B) or non-covalently (DCTPP1, dCTP pyrophosphatase). Other modified attempts to form soluble prodrugs of this natural product (e.g. carboxylic acid, amino acid esters) resulted in difficult removal of the prodrug group.

11.25.2015 Naturalproductman

J. Med. Chem. paper

Posted in Alzheimer's, Cancer, Diterpene, Epoxides, Medicinal Chemistry, Prodrug | 1 Comment »

Penitrem biosynthesis

Posted by naturalproductman on April 12, 2015

Hideaki Oikawa and co-workers at Hokkaido University have reported in ACIE on the enzymatic biosynthesis of penitrem.

alkaloid

ACIE paper

Posted in Biosynthesis, Cyclobutanes, Diterpene, Enzymes, Indoles | Leave a Comment »

Rules are made to be broken

Posted by naturalproductman on May 6, 2014

Craig Williams and co-workers from the University of Queensland have reported in ACIE on the isolation of EBC-219, a diterpene possessing a bridge head olefin.

 
bridgehead

ACIE paper

Posted in Bredt's, Classical rules, Diterpene | Leave a Comment »

Paxilline biosynthesis

Posted by naturalproductman on January 17, 2013

Hideaki Oikawa and co-workers at Hokkaido University have reported in JACS on a biosynthesis study of paxilline.

paxilline

JACS paper

Posted in Alkaloids, Chemical Biology, Diterpene, Indoles | Leave a Comment »

Cubitene synthesis

Posted by naturalproductman on October 2, 2012

Thomas Lindel and co-workers at Technische Universitat Braunschweig have reported in ACIE on the synthesis of cubitene.

cubitene

ACIE paper

Posted in Diterpene, Methodology, Total Synthesis | Leave a Comment »

Erogorgiaene synthesis

Posted by naturalproductman on January 25, 2012

Jhillu Yadav and co-workers at CSIR–Indian Institute of Chemical Technology have reported in European JOC on the synthesis of erogorgiaene.

synthesis
European JOC paper

Posted in Diterpene, Methodology, Total Synthesis | Leave a Comment »

Daphnane diterpenes

Posted by naturalproductman on January 21, 2012

Matthias Hamburger and co-workers from the University of Basel in Switzerland have reported in JNP on the anti-HIV activities of some daphnane derived natural products.

HIV

JNP paper

Posted in Daphnane, Diseases, Diterpene, HIV | Leave a Comment »

Cyclomyrsinane

Posted by naturalproductman on January 4, 2012

Judit Hohmann and co-workers at the University of Szeged in Hungary have reported in Tetrahedron on the isolation of

cyclomyrsinane

Tetrahedron paper

Posted in Diterpene | Leave a Comment »

Atropurpuran progress

Posted by naturalproductman on December 14, 2011

Richard Hsung and co-workers have reported in Organic Letters on their progress towards atropurpuran.

atropurpuran

OL paper

Posted in Allenes, Diterpene, Electrocyclization, Methodology, Pericyclic reactions | Leave a Comment »

Obtusinone A

Posted by naturalproductman on December 11, 2011

Chatchanok Karalai and co-workers at Prince of Songkla University have reported in Tetrahedron on an diterpene with anti-inflammatory properties.

obtusinone

Tetrahedron paper

Posted in Anti-inflammatory, Antibiotics, Diterpene | Leave a Comment »

 
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