Naturalproductman’s Blog

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Archive for the ‘Taxanes’ Category

Taxane synthesis

Posted by naturalproductman on January 4, 2012

Phil Baran and co-workers have reported in Nature Chemistry on the synthesis of the 6,8,6-ring system of taxanes by taking advantage of an intramolecular Diels-Alder reaction.

 

Nature Chemistry paper

Posted in Asymmetric, Cancer, Cycloaddition, Diels-Alder, Methodology, Named Reactions, Pericyclic reactions, Taxanes | Leave a Comment »

Cascade for Taxol

Posted by naturalproductman on March 4, 2011

Jean Suffert and co-workers at CNRS have reported on a palladium catalyzed cascade reaction to ultimately form the taxol ring system.

taxol

 

ACIEE paper

Posted in Cascade Reactions, Electrocyclization, Methodology, Palladium, Pericyclic reactions, Taxanes, Transition Metal, Unnatural Products | Leave a Comment »

Ring Contraction of Taxol

Posted by naturalproductman on March 22, 2010

T. Narender and co-workers at the Central Drug Research Institute in India have recently reported in the Journal of Natural Products of all places, on a novel contraction of the six membered ring in taxol to a five membered ring using BF3 etherate.

ring contraction

JNP paper

Posted in C-C Bond Breaking, C-X Bond Breaking, Methodology, Ring contraction, Taxanes | Leave a Comment »

Taxol Studies

Posted by naturalproductman on March 16, 2010

Rudiger Kaspera, Rodney Croteau and co-workers at Washington State University have recently published in Tetrahedron Letters on an in vitro study of taxol’s oxetane ring formation by synthesizing radiolabeled potential taxol substrates.  However, none of the surrogate substrates synthesized underwent rearrangement to form the oxetane ring.

taxol

TL paper

Posted in Chemical Biology, Mechanistic, Methodology, Taxanes | Leave a Comment »

A New Approach To Taxol

Posted by naturalproductman on July 17, 2009

Gerald Pattenden at the University of Nottingham has recently published in Tetrahedron on an intramolecular radical cyclization approach to access the 8,6-ring system of taxol starting from an alkynyl ketone, enone and a terminal iodide functionalities in the starting material.

taxol

Tetrahedron paper

Posted in Cascade Reactions, Methodology, Radical Chemistry, Ring forming, Taxanes | Leave a Comment »

 
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