A Total Synthesis of Taxol (pages 1723–1726)
John J. Masters, J. T. Link, Lawrence B. Snyder, Wendy B. Young and Prof. Samuel J. Danishefsky
Article first published online: 22 DEC 2003 | DOI: 10.1002/anie.199517231
The intramolecular Heck reaction of 1 to 2 is the cornerstone of this total synthesis of taxol (see conversion below). The route starts with the (S)-Wieland Miescher ketone, and the oxetane ring is installed early in the synthesis. Elaboration to a CD ring fragment, addition of an A ring nucleophile, and further manipulations yield the appropriate starting material (1) for the Heck reaction. After this key step yielding 2, the synthesis of baccatin III (and thence taxol) concludes with the cleavage of the exo double bond at C-10 and oxygenation at C-9 and C-13.