Naturalproductman’s Blog

Hey, is that a natural product?!

Archive for the ‘Diterpene’ Category

Darwinolide

Posted by naturalproductman on May 30, 2016

Bill Baker and co-workers at the University of South Florida have reported in Organic Letters on the isolation of darwinolide from an antarctic sponge that inhibited methicillin-resistant S. aureus biofilm formation.

 

OL paper

Posted in Antibiotics, Diterpene, Lactones | Leave a Comment »

Phorbol synthesis

Posted by naturalproductman on March 31, 2016

Phil Baran and co-workers reported in Nature on a synthesis of phorbol – in 19 steps.

 

Nature paper

Posted in Diterpene, Total Synthesis | Leave a Comment »

Conidiogenone, conidiogenol, and conidiogenone B syntheses

Posted by naturalproductman on March 7, 2016

Yong-Qiang Tu and co-workers from Lanzhou University have reported in ACIE on the syntheses of conidiogenone, conidiogenol, and conidiogenone B.

ACIE paper

Posted in Diterpene, Total Synthesis | Leave a Comment »

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 »