Scalable Enantioselective Total Synthesis of Taxanes
(Section 1.6)

Transformation of (+)-17 to Taxadienone

Story:

         Dr. Masato Ketchum is vigorously working in his laboratory in Kanto trying to synthesize the fiercest Pokemon to every walk on the face of this Earth. He has been working on this for months and he thinks he has figured out how he can utilize an ancient Pokemon, Mew or Molecule (+)-17, to create a ferocious Mewtwo (Taxadienone or (+)-6). Recently, Dr. Ketchum has finally found a breakthrough. In a sudden moment of clarity, he exclaims, "all I need to to do is use Pd(PPh₃)₄ and use my arch rival's Negishi coupling method to create the ultimate Pokemon. I should have thought of this a long time ago!” As Dr. Ketchum synthesizes Mewtwo he creates an intermediate Pokemon which has an enol triflate, after Pd(PPh₃)₄ is added.

Mew and Mewtwo

Abstract:

        The above molecules are part of a study to more efficiently synthesize taxanes. Specifically, the above molecules are part of a multi-step synthesis of taxadiene, a parent taxane that can be used to synthesize other taxanes such as Taxol, a billion-dollar anticancer drug. Taxol is currently synthesized from cell-cultures and this study endeavors to create a reaction that can synthesize Taxol chemically and commercially on a grand scale. The chemistry involved in forming these molecules includes Diels-Alder reactions, enol triflate formation, and Negishi coupling.¹