The Nicolaou Taxol total synthesis, published by K. C. Nicolaou and his group in 1994 concerns the total synthesis of Taxol. This organic synthesis was included in Nicolaou's book, 'Classics in Total Synthesis'. Taxol is an important drug in the treatment of cancer but also expensive because the compound is harvested from a scarce resource, namely the pacific yew.
This synthetic route to Taxol is one of several; other groups have presented their own solutions, notably the group of Holton with a linear synthesis starting from borneol, the Samuel Danishefsky group starting from the Wieland-Miescher ketone and the Wender group from pinene.
The Nicolaou synthesis is a good example of convergent synthesis because the molecule is assembled from 3 pre-assembled synthons. Two major parts are cyclohexene rings A and C that are connected by two short bridges creating an 8 membered ring in the middle (ring B). The third pre-assembled part is an amide tail. Ring D is an oxetane ring fused to ring C. Two key chemical transformations are the Shapiro reaction and the pinacol coupling reaction. The overall synthesis was published in 1995 in a series of four papers in the Journal of the American Chemical Society.
Read more about Nicolaou Taxol Total Synthesis: Retrosynthesis, C Ring Synthesis, A Ring Synthesis, B Ring Synthesis, Resolution, D Ring Synthesis, Tail Addition
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