Synthesis of pseudo-AB ring analogues of Taxol

A review regarding the discovery and development of the clinical drug Paclitaxel (Taxol®) and the representative chemical syntheses of this natural product from 1960 to 2003 are given in this thesis.; A synthesis of the pseudo-AB ring analogue of paclitaxel is described. My synthetic studies revealed that the Diels Alder reaction of S-(+)-carvone and isoprene could afford a bicyclic system which was successfully elaborated to form the CD ring of taxol. A crucial intermediate in the synthetic pathway was selected for further manipulation to the pseudo-core of taxol involving a Baeyer-Villiger reaction, an Oppenaurer oxidation and Merrwein-Ponndorf-Verley reduction, a stereospecific Grignard addition, a selective debenzylation, a selective benzylic oxidation and an intramolecular S_N2 reaction as the key steps.; Moreover, the synthesis of the side chain of taxol was accomplished via an asymmetric epoxidation of cis-ethyl cinnamate with an ulose catalyst.; Finally, the coupling of the pseudo-core of taxol with the side chain afforded the protected pseudo-AB ring analogue of taxol.