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Taxanes form a large family of terpenes comprising over 350 members, the most famous of which is Taxol (paclitaxel), a billion-dollar anticancer drug. Here, we describe the first practical and scalable synthetic entry to these natural products via a concise preparation of (+)-taxa-4(5),11(12)-dien-2-one, which has a suitable functional handle with which to access more oxidized members of its family. This route enables a gram-scale preparation of the 'parent' taxane--taxadiene--which is the largest quantity of this naturally occurring terpene ever isolated or prepared in pure form. The characteristic 6-8-6 tricyclic system of the taxane family, containing a bridgehead alkene, is forged via a vicinal difunctionalization/Diels-Alder strategy. Asymmetry is introduced by means of an enantioselective conjugate addition that forms an all-carbon quaternary centre, from which all other stereocentres are fixed through substrate control. This study lays a critical foundation for a planned access to minimally oxidized taxane analogues and a scalable laboratory preparation of Taxol itself.

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In early 2012, we reported the gram-scale synthesis of a non-natural taxane, taxadienone, as well as that of a natural taxane, taxadiene. Now, chemists at Albany Molecular Research Inc. (AMRI) report a route optimization of taxadienone in none other than the...
Baran, Mendoza, Ishihara. Nature Chem., 2011, EarlyView. DOI: 10.1038/nchem.1196 Hmm… I’m still not convinced about whether I should really post on this paper, but I’m interested in it, so to hell with the rules! What we’ve got here...
The taxanes are a large family of 350 or so natural products, of which the best known is taxol itself, a multibillion dollar anticancer drug with a rich and storied history, whose name and distinctive tetracyclic system are instantly recognisable to most organic...