Paclitaxel analogues with a thiol group in place of the hydroxyl group on the C-13 side chain constitute an interesting avenue of research for the study of new taxoid compounds. A synthetic route for the preparation of the exact thiol surrogate product of Taxol® by coupling (4S, 5S)-2,4-diphenyloxazoline-5-carboxylic acid with 7-triethylsilyl baccatin III, followed by ring-opening of the oxazoline intermediate with thiolacetic acid is described.
Bibliographical noteFunding Information:
We thank Hanmi Pharmaceutical Co., Ltd for the generous donation of 10-deacetylbaccatin III. This work was supported by Korea Science and Engineering Foundation (R14-2003-014-01001-0) and the Brain Korea 21 Program.