ChemInform Abstract: Modified Taxols. Part 3. Preparation and Acylation of Baccatin III (I).

Samarium Diiodide-Mediated Deoxygenation of Taxol: A One-Step Synthesis of 10-Deacetoxytaxol

“…Our initial investigations involved modifications of baccatin III (3), a more readily available diterpene18, 19 which can be converted to taxol (1) in a few steps. 20,21 Treatment of a THF solution of baccatin III (3) with SmL,22 in the presence of ieri-butyl alcohol for 15 h, produced 10-deacetoxybaccatin III (5) in 45% yield together with about 40% of a 2:1 mixture23 of 10-deacetoxy-7-ep¿-baccatin III (Figure 1, 7)24 and 10-deacetoxy-7-epi-13-oxobaccatin III (Figure 1,8).…”