The taxane family is one of the most challenging synthetic targets due to their unique carbon skeleton coupled with the highly potent anticancer activities of a congener, taxol. We have developed a powerful methodology based on Lewis acid mediated direct eight-membered-ring cyclization for taxane B ring that offers a general route for natural taxane synthesis. The methodology provides simultaneous solution for the following three of the most difficult problems for taxane synthesis.
1) construction of the highly strained eight-membered B ring
2) stereoselective installation of the C-9 and C-10 oxygen functionalities
3) stereocontrol of the endo conformation.